Herbicidal conposition

ABSTRACT

Herbicidal composition that, in addition to comprising customary inert formulation adjuvants, comprises a) a compound of formula (I), wherein the substituents are as defined in claim 1, or an agronomically acceptable salt of that compound, and b) a synergistically effective amount of one or mote compounds of formulae 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, dliclofop-methyl, amidosulfuron, flupyr-sulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribe-nuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlor-prop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin. The compositions according to the invention may also comprise a safener.

The present invention relates to a novel herbicidal composition comprising a herbicidal active ingredient combination that is suitable for the selective control of weeds in crops of useful plants, for example in crops of maize. The invention relates also to a method of controlling weeds in crops of useful plants and to the use of the novel composition for that purpose.

The compounds of formula I

wherein

-   p is 0 or 1; -   R₁ is a C₁-C₆alkylene, C₃-C₆alkenylene or C₃-C₆alkynylene chain,     which may be substituted one or more times by halogen or by R₅, the     unsaturated bonds of the chain not being attached directly to the     substituent X₁; -   X₁ is oxygen, —O(CO)—, —(CO)O—, —O(CO)O—, —N(R₆)—O—, —O—NR₅₁—, thio,     sulfinyl, sulfonyl, —SO₂NR₇—, —NR₅₂SO₂— or —NR₈—; -   R₂ is a C₁-C₈alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which is     substituted one or more times by halogen, hydroxy, amino, formyl,     nitro, cyano, mercapto, carbamoyl, C₁-C₆alkoxy, C₁-C₆alkoxycarbonyl,     C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl,     C₃-C₆-cycloalkyl, halo-substituted C₃-C₆cycloalkyl, C₃-C₆alkenyloxy,     C₃-C₆alkynyloxy, C₁-C₆halo-alkoxy, C₃-C₆haloalkenyloxy,     cyano-C₁-C₆alkoxy, C₁-C₆alkoxy-C₁-C₆alkoxy,     C₁-C₆alkoxy-C₁-C₆alkoxy-C₁-C₆alkoxy, C₁-C₆alkylthio-C₁-C₆alkoxy,     C₁-C₆alkylsulfinyl-C₁-C₆alkoxy, C₁-C₆-alkylsulfonyl-C₁-C₆alkoxy,     C₁-C₆alkoxycarbonyl-C₁-C₆alkoxy, C₁-C₆alkoxycarbonyl,     C₁-C₆-alkylcarbonyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,     C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,     C₁-C₆haloalkylsulfonyl, oxiranyl (which may in turn be substituted     by C₁-C₆alkyl), (3-oxetanyl)-oxy (which may in turn be substituted     by C₁-C₆alkyl), benzylthio, benzylsulfinyl, benzylsulfonyl,     C₁-C₆alkylamino, di(C₁-C₆alkyl)amino, R₉S(O)₂O, R₁₀N(R₁₁)SO₂—,     rhodano, phenyl, phenoxy, phenylthio, phenylsulfinyl or by     phenylsulfonyl; wherein the phenyl- or benzyl-containing groups may     in turn be substituted by one or more C₁-C₆alkyl, C₁-C₆haloalkyl,     C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or nitro     groups, or -   R₂ is phenyl, which may be substituted one or more times by     C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen,     cyano, hydroxy or by nitro; or -   R₂ is C₃-C₆cycloalkyl; C₃-C₆cycloalkyl substituted by C₁-C₆alkoxy or     by C₁-C₆alkyl; 3-oxetanyl or 3-oxetanyl substituted by C₁-C₆alkyl; -   or, when Q is Q₂ or Q₃, or when Q is Q₁ wherein R₁₄ and R₂₂ denote a     C₂-C₃alkylene chain, R₂ may additionally be a five- to ten-membered,     monocyclic or fused bicyclic ring system, which may be aromatic,     saturated or partially saturated and which may contain from 1 to 4     hetero atoms selected from nitrogen, oxygen and sulfur, the ring     system being bonded to the substituent X, directly or via a     C₁-C₄alkylene, C₂-C₄alkenyl-C₁-C₄alkylene,     C₂-C₄alkynyl-C₁-C₄alkylene, —N(R₁₂)—C₁-C₄alkylene, —SO—C₁-C₄alkylene     or —SO₂—C₁-C₄alkylene group, and wherein each ring system may     contain no more than two oxygen atoms and no more than two sulfur     atoms and the ring system may itself be mono-, di- or     tri-substituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl,     C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₁-C₆alkoxy,     hydroxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy,     mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio,     C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio,     C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio,     C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,     C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl,     C₁-C₂alkylaminosulfonyl, di(C₁-C₂alkyl)aminosulfonyl,     di(C₁-C₄alkyl)amino, halogen, cyano, nitro, phenyl or by benzylthio,     wherein phenyl and benzylthio may in turn be substituted on the     phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,     C₁-C₃haloalkoxy, halogen, cyano or by nitro, and wherein the     substituents on the nitrogen in the heterocyclic ring are other than     halogen; or -   R₂ is hydrogen or unsubstituted C₁-C₈alkyl, when either -   a) R₁ is substituted by the group R₅, or -   b) Q is the group Q₂, or -   c) Q is the group Q₃ wherein X, is —O(CO)—, —(CO)O—, —N(R₆)—O—,     —O—NR₅₁—, —SO₂NR₇—, —NR₅₂SO₂— or —NR₈—; or -   d) Q is the group Q₁ wherein X₁ is —N(R₆)—O—, —O—NR₅₁—, —SO₂NR₇—,     —NR₅₂SO₂— or —NR₈—, or -   e) Q is the group Q₁ wherein R₁₄ and R₂₂ in Q₁ denote a     C₂-C₃alkylene chain and X₁ is —O(CO)— or —(CO)O—; -   R₃ is C₁-C₃haloalkyl; -   R₄ is hydrogen, halogen, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,     C₁-C₃alkoxy-C₁-C₃alkyl or C₁-C₃alkoxy-C₁-C₃alkoxy; -   R₅ is hydroxy, C₁-C₆alkoxy, C₃-C₆cycloalkyloxy,     C₁-C₆alkoxy-C₁-C₆alkoxy, C₁-C₆alkoxy-C₁-C₆alkoxy-C₁-C₆alkoxy or     C₁-C₂alkylsulfonyloxy; -   R₆, R₇, R₈, R₉, R₁₀, R₁1, R₁₂, R₅₁ and R₅₂ are each independently of     the others hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl,     C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxy-C₁-C₆alkyl,     C₁-C₆alkoxy-C₁-C₆alkyl substituted by C₁-C₆alkoxy, benzyl, or     phenyl, wherein phenyl and benzyl may in turn be substituted one or     more times by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆-alkoxy,     C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; wherein R₆ is     not hydrogen when R₉ is hydrogen, C₁-C₆alkoxycarbonyl or     C₁-C₆alkylcarbonyl; -   Q is Q₁     wherein -   A₁ is C(R₁₄R₁₅), NR₁₆ or oxygen; -   A₂ is C(R₁₇R₁₈), C(O), —C═N—O—R₁₉, oxygen, thio, sulfinyl, sulfonyl,     —NR₂₀ or ethylene; with the provisos that A₁ is other than oxygen     when A₂ is oxygen, C(O), thio, sulfinyl, —C═N—O—R₁₉, NR₂₀ or     C(R₁₇R₁₈), R₁₇ and R₁₈ being each independently of the other     C₁-C₄alkoxy, C₁-C₄-alkylthio, C₁-C₄alkylsulfinyl or     C₁-C₄alkylsulfonyl; and that A₁ is other than NR₁₆ when A₂ is thio,     sulfinyl or C(R₁₇R₁₈), R₁₇ and R₁₈ being each independently of the     other C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or     C₁-C₄alkylsulfonyl; -   R₁₄ and R₂₂ are each independently of the other hydrogen,     C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₄-alkenyl, C₃-C₄alkynyl,     C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,     C₁-C₄alkylsulfonyl-oxy, C₁-C₄alkoxy, C₁-C₄alkoxycarbonyl or     C₁-C₄alkylcarbonyl; -   R₁₅ and R₂₁ are each independently of the other hydrogen,     C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₄-alkenyl or C₃-C₄alkynyl; -   R₁₇ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,     C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or C₁-C₄alkylsulfonyl; -   R₁₈ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₄alkenyl,     C₃-C₄alkynyl, C₁-C₄alkoxy, C₁-C₄-alkylthio, C₁-C₄alkylsulfinyl,     C₁-C₄alkylsulfonyl or di(C₁-C₄)alkoxyalkyl-C₁-C₄alkyl; -   R₂₀ is C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl,     C₁-C₄alkylcarbonyl, C₁-C₄alkyl-carbonyloxy,     di(C₁-C₄)alkylaminocarbonyl or benzyl, wherein the phenyl group may     be substituted one or more times by C₁-C₆alkyl, C₁-C₆haloalkyl,     C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; -   R₁₉ and R₁₆ are each independently of the other hydrogen,     C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl, benzyl or     phenyl, wherein phenyl and benzyl may in turn be substituted one or     more times by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,     C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; -   or R₁₄ and R₂₂ together form a C₂-C₃alkylene chain; -   or R₁₄ and R₁₅ together and/or R₁₇ and R₁₈ together and/or R₂₁ and     R₂₂ together form a C₂-C₄alkylene chain, which may be interrupted by     oxygen and/or by carbonyl and/or by sulfur, with the proviso that     the oxygen and sulfur atoms are separated by at least one methylene     group; -   or R₁₄ and R₁₈ together form a C₂-C₄alkylene chain; or -   R₂₂ and R₁₆ together form a C₂-C₄alkylene chain; -   or R₁₈ forms, together with R₂₂ or R₁₄, a direct bond; -   or R₁₆ and R₁₈ together form a C₂-C₄alkylene chain; -   R₁₃ is hydroxy; O⁻M⁺ wherein M⁺ is an alkali metal cation or an     ammonium cation; halogen, C₁-C₁₂alkylsulfonyloxy, amino,     C₁-C₄alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl,     C₁-C₁₂-haloalkylthio, C₁-C₁₂haloalkylsulfinyl,     C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio,     C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl,     C₃-C₁₂alkenylthio, C₃-C₁₂-alkenylsulfinyl, C₃-C₁₂alkenylsulfonyl,     C₃-C₁₂alkynylthio, C₃-C₁₂alkynylsulfinyl, C₃-C₁₂alkynyl-sulfonyl,     C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio,     C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl,     C₁-C₄-alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O,     C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₂₃R₂₄N,     R₂₅R₂₆NNH, R₂₇R₂₈NC(O)O—, R₂₉R₃₀NC(O)NH—, C₁-C₁₈alkyl-carbonyloxy,     C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy,     C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy,     C₁-C₁₂alkylthiocarbonyloxy or C₁-C₁₂alkylthiocarbamoyl, wherein the     alkyl, alkenyl and alkynyl groups may be substituted by halogen,     C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl     or by cyano; -   or R₁₃ is phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl,     phenylsulfonylamino, phenyl-sulfonyloxy or benzoyloxy, wherein the     phenyl groups may in turn be substituted by one or more halogen,     nitro, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy or     C₁-C₄haloalkoxy groups; -   or R₁₃ is a group Het₁-thio, Het₂-sulfinyl, Het₃-sulfonyl,     Het₄-(CO)O or Het₅-N(R₃₃); wherein Het₁, Het₂, Het₃, Het₄ and Het₅     are each independently of the others a five- to ten-membered,     monocyclic or fused bicyclic ring system, which may be aromatic or     partially saturated and which may contain from 1 to 4 hetero atoms     selected from nitrogen, oxygen and sulfur and wherein each ring     system may contain no more than two oxygen atoms and no more than     two sulfur atoms and the ring system may itself be substituted by     C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,     C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,     di(C₁-C₄alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano,     nitro or by phenyl, and wherein the substituents on the nitrogen in     the heterocyclic ring are other than halogen; -   R₂₃, R₂₄, R₂₅, R₂₆, R₂₇, R₂₈, R₂₉, R₃₀ and R₃₃ are each     independently of the others hydrogen or C₁-C₆alkyl; -   or R₂₃ and R₂₄ together or R₂₅ and R₂₆ together or R₂₇ and R₂₈     together or R₂₉ and R₃₀ together are pyrrolidino, piperidino,     morpholino or thiomorpholino, each of which may be mono- or     poly-substituted by methyl groups; -   or Q is Q₂     wherein -   R₃₄ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl,     C₂-C₄alkenyl, C₂-C₄alkynyl or benzyl, wherein the phenyl group may     be substituted one or more times by C₁-C₆alkyl, C₁-C₆haloalkyl,     C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; -   R₃₅ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl,     C₃-C₄alkenyl, C₃-C₄alkynyl or benzyl; wherein the phenyl group may     be substituted one or more times by C₁-C₆alkyl, C₁-C₆haloalkyl,     C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; -   R₃₆ is hydroxy; O⁻M⁺wherein M⁺is an alkali metal cation or an     ammonium cation; halogen, C₁-C₁₂alkylsulfonyloxy, amino,     C₁-C₄alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl,     C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl,     C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkyl-thio,     C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl,     C₃-C₁₂alkenylthio, C₃-C₁₂alkenylsulfinyl, C₃-C₁₂alkenylsulfonyl,     C₃-C₁₂alkynylthio, C₃-C₁₂alkynylsulfinyl, C₃-C₁₂alkynylsulfonyl,     C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio,     C₁-C₄alkoxycarbonyl-C₁-C₄alkyl-sulfinyl,     C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O,     C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₃₇R₃₈N,     R₃₉R₄₀NNH, R₄₁R₄₂NC(O)O—, R₄₃R₄₄NC(O)NH—, C₁-C₁₈alkylcarbonyloxy,     C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₆alkynylcarbonyloxy,     C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy,     C₁-C₁₂alkylthiocarbonyloxy or C₁-C₁₂alkylthiocarbamoyl, wherein the     alkyl, alkenyl and alkynyl groups may be substituted by halogen,     C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl     or by cyano; or R₃₆ is phenoxy, phenylthio, phenylsulfinyl,     phenylsulfonyl, phenylsulfonylamino, phenyl-sulfonyloxy or     benzoyloxy, wherein the phenyl groups may in turn be substituted one     or more times by halogen, nitro, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl,     C₁-C₄alkoxy or by C₁-C₄halo-alkoxy, -   or R₃₆ is a group Het₇-thio, Het₈-sulfinyl, Het₉-sulfonyl,     Het₁₀-(CO)O or Het₁₁-N(R₄₇); wherein Het₇, Het₈, Het₉, Het₁₀ and     Het₁₁ are each independently of the others a five- to ten-membered,     monocyclic or fused bicyclic ring system, which may be aromatic or     partially saturated and which may contain from 1 to 4 hetero atoms     selected from nitrogen, oxygen and sulfur and wherein each ring     system may contain no more than two oxygen atoms and no more than     two sulfur atoms and the ring system may itself be substituted by     C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,     C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkyl-sulfonyl,     di(C₁-C₄alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano,     nitro or by phenyl, and wherein the substituents on the nitrogen in     the heterocyclic ring are other than halogen; R₃₇, R₃₈, R₃₉, R₄₀,     R₄₁, R₄₂, R₄₃, R₄₄ and R₄₇ are each independently of the others     hydrogen or C₁-C₆alkyl; or -   R₃₇ and R₃₈ together or R₃₉ and R₄₀ together or R₄₁ and R₄₂ together     or R₄₃ and R₄₄ together are pyrrolidino, piperidino, morpholino or     thiomorpholino, each of which may be mono- or poly-substituted by     methyl groups; -   or Q is Q₃     wherein -   R₄₉ is C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl or     halo-substituted C₃-C₆cycloalkyl; -   R₅₀ is C₁-C₃alkylene, which may be substituted by halogen, hydroxy,     C₁-C₆alkoxy, C₂-C₆-alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl,     C₁-C₆alkoxy-C₁-C₆alkoxy, C₁-C₆alkoxy-C₁-C₆alkoxy-C₁-C₆alkoxy,     (3-oxetanyl)-oxy, or by (3-oxetanyl)-oxy substituted by C₁-C₆alkyl,     or by benzylthio, benzylsulfinyl, benzylsulfonyl, phenyl, phenoxy,     phenylthio, phenylsulfinyl or by phenylsulfonyl, wherein the phenyl-     and benzyl-containing groups may in turn be substituted by one or     more C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,     halogen, cyano, hydroxy or nitro groups; -   or R₅₀ is phenyl, wherein the phenyl-containing group may in turn be     substituted by one or more C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,     C₁-C₆haloalkoxy, halogen, cyano, hydroxy or nitro substituents, -   or R₅₀ is C₃-C₆cycloalkyl, C₃-C₆cycloalkyl substituted by     C₁-C₆alkoxy or by C₁-C₆alkyl, 3-oxetanyl or 3-oxetanyl substituted     by C₁-C₆alkyl; and -   n is 0, 1 or 2; and also agronomically acceptable     salts/N-oxides/isomers/enantiomers of such compounds except for the     compound     4-hydroxy-3-[2-(2-methoxyethoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonyl]-bicyclo[3.2.1]oct-3-en-2-one,     and with the provisos that —R₁—X, —R₂ is other than     C₁-C₄alkoxy-C₁-C₄alkoxy-C₁-C₄alkyl when -   a) Q is Q, wherein A₁ is C(R₁₄R₁₅) and A₂ is C(R₁₇R₁₈), R₁₅, R₁₇ and     R₁₈ are hydrogen and R₁₄ and R₂₂ together form a C₂-C₃alkylene     chain; and when -   b) Q is Q₁, R₁₄ and R₂₂ do not together form a C₂-C₃alkylene chain,     A₁ is C(R₁₄R₁₅), or A₁ is NR₁₆ and A₂ is oxygen; and when -   c) Q is Q₃, exhibit herbicidal action.

The compounds of formula I and their preparation are known, for example, from WO 01/94339. The compounds of formula I can also be prepared by methods known per se described, for example, in WO 97/46530 or WO 00/15615 or WO 00/39094.

Surprisingly, it has now been found that a combination of variable amounts of active ingredients, that is to say a compound of formula I together with one or more of the active ingredients indicated below, which are known and some of which are also commercially available, exhibits a synergistic action that is capable of controlling, both pre-emergence and post-emergence, the majority of weeds occurring especially in crops of useful plants.

There is therefore proposed in accordance with the present invention a novel synergistic composition for the selective control of weeds which, in addition to comprising customary inert formulation adjuvants, comprises as active ingredient a mixture of

-   a) a herbicidally effective amount of a compound of formula I     wherein -   p is 0 or 1; -   R₁ is a C₁-C₆alkylene, C₃-C₆alkenylene or C₃-C₆alkynylene chain,     which may be substituted one or more times by halogen or by R₅, the     unsaturated bonds of the chain not being attached directly to the     substituent X₁; -   X₁ is oxygen, —O(CO)—, —(CO)O—, —O(CO)O—, —N(R₆)—O—, —O—NR₅₁—, thio,     sulfinyl, sulfonyl, —SO₂NR₇—, —NR₅₂SO₂— or —NR₈—; -   R₂ is a C₁-C₈alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which is     substituted one or more times by halogen, hydroxy, amino, formyl,     nitro, cyano, mercapto, carbamoyl, C₁-C₆alkoxy, C₁-C₆alkoxycarbonyl,     C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl,     C₃-C₆-cycloalkyl, halo-substituted C₃-C₆cycloalkyl, C₃-C₆alkenyloxy,     C₃-C₆alkynyloxy, C₁-C₆halo-alkoxy, C₃-C₆haloalkenyloxy,     cyano-C₁-C₆alkoxy, C₁-C₆alkoxy-C₁-C₆alkoxy,     C₁-C₆alkoxy-C₁-C₆alkoxy-C₁-C₆alkoxy, C₁-C₆alkylthio-C₁-C₆alkoxy,     C₁-C₆alkylsulfinyl-C₁-C₆alkoxy, C₁-C₆-alkylsulfonyl-C₁-C₆alkoxy,     C₁-C₆alkoxycarbonyl-C₁-C₆alkoxy, C₁-C₆alkoxycarbonyl,     C₁-C₆-alkylcarbonyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,     C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,     C₁-C₆haloalkylsulfonyl, oxiranyl (which may in turn be substituted     by C₁-C₆alkyl), (3-oxetanyl)-oxy (which may in turn be substituted     by C₁-C₆alkyl), benzylthio, benzylsulfinyl, benzylsulfonyl,     C₁-C₆alkylamino, di(C₁-C₆alkyl)amino, R₉S(O)₂O, R₁₀N(R₁₁)SO₂—,     rhodano, phenyl, phenoxy, phenylthio, phenylsulfinyl or by     phenylsulfonyl; wherein the phenyl- or benzyl-containing groups may     in turn be substituted by one or more C₁-C₆alkyl, C₁-C₆haloalkyl,     C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or nitro     groups, or -   R₂ is phenyl, which may be substituted one or more times by     C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen,     cyano, hydroxy or by nitro; or -   R₂ is C₃-C₆cycloalkyl; C₃-C₆cycloalkyl substituted by C₁-C₆alkoxy or     by C₁-C₆alkyl; 3-oxetanyl or 3-oxetanyl substituted by C₁-C₆alkyl; -   or, when Q is O₂ or Q₃, or when Q is Q, wherein R₁₄ and R₂₂ denote a     C₂-C₃alkylene chain, R₂ is additionally a five- to ten-membered,     monocyclic or fused bicyclic ring system, which may be aromatic,     saturated or partially saturated and which may contain from 1 to 4     hetero atoms selected from nitrogen, oxygen and sulfur, the ring     system being bonded to the substituent X₁ directly or via a     C₁-C₄alkylene, C₂-C₄alkenyl-C₁-C₄alkylene,     C₂-C₄alkynyl-C₁-C₄alkylene, —N(R₁₂)—C₁-C₄alkylene, —SO—C₁-C₄alkylene     or —SO₂—C₁-C₄alkylene group, and wherein each ring system may     contain no more than two oxygen atoms and no more than two sulfur     atoms and the ring system may itself be mono-, di- or     tri-substituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl,     C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₁-C₆alkoxy,     hydroxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy,     mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio,     C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio,     C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio,     C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,     C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl,     C₁-C₂alkylaminosulfonyl, di(C₁-C₂alkyl)aminosulfonyl,     di(C₁-C₄alkyl)amino, halogen, cyano, nitro, phenyl or by benzylthio,     wherein phenyl and benzylthio may in turn be substituted on the     phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,     C₁-C₃haloalkoxy, halogen, cyano or by nitro, and wherein the     substituents on the nitrogen in the heterocyclic ring are other than     halogen; or -   R₂ is hydrogen or unsubstituted C₁-C₈alkyl, when either -   a) R₁ is substituted by the group R₅, or -   b) Q is the group Q₂, or -   c) Q is the group Q₃ wherein X₁ is —O(CO)—, —(CO)O—, —N(R₆)—O—,     —O—NR₅₁—, —SO₂NR₇—, —NR₅₂SO₂— or —NR₈—; or -   d) Q is the group Q₁ wherein X₁ is —N(R₆)—O—, —O—NR₅₁—, —SO₂NR₇—,     —NR₅₂SO₂— or —NR₈—, or -   e) Q is the group Q₁ wherein R₁₄ and R₂₂ in Q₁ denote a     C₂-C₃alkylene chain and X₁ is —O(CO)— or —(CO)O—; -   R₃ is C₁-C₃haloalkyl; -   R₄ is hydrogen, halogen, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,     C₁-C₃alkoxy-C₁-C₃alkyl or C₁-C₃alkoxy-C₁-C₃alkoxy; -   R₅ is hydroxy, C₁-C₆alkoxy, C₃-C₆Cycloalkyloxy,     C₁-C₆alkoxy-C₁-C₆alkoxy, C₁-C₆alkoxy-C₁-C₆alkoxy-C₁-C₆alkoxy or     C₁-C₂alkylsulfonyloxy; -   R₆, R₇, R₈, R₉, R₁₀, R₁₁, R₁₂, R₅₁ and R₅₂ are each independently of     the others hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl,     C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxy-C₁-C₆alkyl,     C₁-C₆alkoxy-C₁-C₆alkyl substituted by C₁-C₆alkoxy, benzyl, or     phenyl, wherein phenyl and benzyl may in turn be substituted one or     more times by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆-alkoxy,     C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; wherein R₆ is     not hydrogen when R₉ is hydrogen, C₁-C₆alkoxycarbonyl or     C₁-C₆alkylcarbonyl; -   Q is Q₁     wherein -   A₁ is C(R₁₄R₁₅), NR₁₆ or oxygen; -   A₂ is C(R₁₇R₁₈), C(O), —C═N—O—R₁₉, oxygen, thio, sulfinyl, sulfonyl,     —NR₂₀ or ethylene; with the provisos that A₁ is other than oxygen     when A₂ is oxygen, C(O), thio, sulfinyl, —C═N—O—R₁₉, NR₂₀ or     C(R₁₇R₁₈), R₁₇ and R₁₈ being each independently of the other     C₁-C₄alkoxy, C₁-C₄-alkylthio, C₁-C₄alkylsulfinyl or     C₁-C₄alkylsulfonyl; and that A₁ is other than NR₁₆ when A₂ is thio,     sulfinyl or C(R₁₇R₁₈), R₁₇ and R₁₈ being each independently of the     other C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or     C₁-C₄alkylsulfonyl; -   R₁₄ and R₂₂ are each independently of the other hydrogen,     C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₄-alkenyl, C₃-C₄alkynyl,     C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,     C₁-C₄alkylsulfonyl-oxy, C₁-C₄alkoxy, C₁-C₄alkoxycarbonyl or     C₁-C₄alkylcarbonyl; -   R₁₅ and R₂₁ are each independently of the other hydrogen,     C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₄-alkenyl or C₃-C₄alkynyl; -   R₁₇ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,     C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or C₁-C₄alkylsulfonyl; -   R₁₈ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₄alkenyl,     C₃-C₄alkynyl, C₁-C₄alkoxy, C₁-C₄-alkylthio, C₁-C₄alkylsulfinyl,     C₁-C₄alkylsulfonyl or di(C₁-C₄)alkoxyalkyl-C₁-C₄alkyl; -   R₂₀ is C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl,     C₁-C₄alkylcarbonyl, C₁-C₄alkyl-carbonyloxy,     di(C₁-C₄)alkylaminocarbonyl or benzyl, wherein the phenyl group may     be substituted one or more times by C₁-C₆alkyl, C₁-C₆haloalkyl,     C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; -   R₁₉ and R₁₆ are each independently of the other hydrogen,     C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl, benzyl or     phenyl, wherein phenyl and benzyl may in turn be substituted one or     more times by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,     C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; -   or R₁₄ and R₂₂ together form a C₂-C₃alkylene chain; -   or R₁₄ and R₁₅ together and/or R₁₇ and R₁₈ together and/or R₂₁ and     R₂₂ together form a C₂-C₄alkylene chain, which may be interrupted by     oxygen and/or by carbonyl and/or by sulfur, with the proviso that     the oxygen and sulfur atoms are separated by at least one methylene     group; -   or R₁₄ and R₁₈ together form a C₂-C₄alkylene chain; or -   R₂₂ and R₁₈ together form a C₂-C₄alkylene chain; -   or R₁₈ forms, together with R₂₂ or R₁₄, a direct bond; -   or R₁₆ and R₁₈ together form a C₂-C₄alkylene chain; -   R₁₃ is hydroxy; O⁻M⁺ wherein M⁺ is an alkali metal cation or an     ammonium cation; halogen, C₁-C₁₂alkylsulfonyloxy, amino,     C₁-C₄alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl,     C₁-C₁₂-haloalkylthio, C₁-C₁₂haloalkylsulfinyl,     C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio,     C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl,     C₃-C₁₂alkenylthio, C₃-C₁₂-alkenylsulfinyl, C₃-C₁₂alkenylsulfonyl,     C₃-C₁₂alkynylthio, C₃-C₁₂alkynylsulfinyl, C₃-C₁₂alkynyl-sulfonyl,     C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio,     C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl,     C₁-C₄-alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O,     C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₂₃R₂₄N,     R₂₅R₂₆NNH, R₂₇R₂₈NC(O)O—, R₂₉R₃₀NC(O)NH—, C₁-C₁₈alkyl-carbonyloxy,     C₂-C₁ alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy,     C₃-C₆cycloalkylcarbonyl-oxy, C₁-C₁₂alkoxycarbonyloxy,     C₁-C₁₂alkylthiocarbonyloxy or C₁-C₁₂alkylthiocarbamoyl, wherein the     alkyl, alkenyl and alkynyl groups may be substituted by halogen,     C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl     or by cyano; -   or R₁₃ is phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl,     phenylsulfonylamino, phenyl-sulfonyloxy or benzoyloxy, wherein the     phenyl groups may in turn be substituted by one or more halogen,     nitro, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy or     C₁-C₄haloalkoxy groups; -   or R₁₃ is a group Het₁-thio, Het₂-sulfinyl, Het₃-sulfonyl,     Het₄-(CO)O or Het₅-N(R₃₃); wherein Het₁, Het₂, Het₃, Het₄ and Het₅     are each independently of the others a five- to ten-membered,     monocyclic or fused bicyclic ring system, which may be aromatic or     partially saturated and which may contain from 1 to 4 hetero atoms     selected from nitrogen, oxygen and sulfur and wherein each ring     system may contain no more than two oxygen atoms and no more than     two sulfur atoms and the ring system may itself be substituted by     C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,     C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,     di(C₁-C₄alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano,     nitro or by phenyl, and wherein the substituents on the nitrogen in     the heterocyclic ring are other than halogen; -   R₂₃, R₂₄, R₂₅, R₂₆, R₂₇, R₂₈, R₂₉, R₃₀ and R₃₃ are each     independently of the others hydrogen or C₁-C₆alkyl; -   or R₂₃ and R₂₄ together or R₂₅ and R₂₆ together or R₂₇ and R₂₈     together or R₂₉ and R₃₀ together are pyrrolidino, piperidino,     morpholino or thiomorpholino, each of which may be mono- or     poly-substituted by methyl groups; -   or Q is Q₂     wherein -   R₃₄ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl,     C₂-C₄alkenyl, C₂-C₄alkynyl or benzyl, wherein the phenyl group may     be substituted one or more times by C₁-C₆alkyl, C₁-C₆haloalkyl,     C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; -   R₃₅ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl,     C₃-C₄alkenyl, C₃-C₄alkynyl or benzyl, wherein the phenyl group may     be substituted one or more times by C₁-C₆alkyl, C₁-C₆haloalkyl,     C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; -   R₃₆ is hydroxy; O⁻M⁺ wherein M⁺ is an alkali metal cation or an     ammonium cation; halogen, C₁-C₁₂alkylsulfonyloxy, amino,     C₁-C₄alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl,     C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl,     C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkyl-thio,     C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl,     C₃-C₁₂alkenylthio, C₃-C₁₂alkenylsulfinyl, C₃-C₁₂alkenylsulfonyl,     C₃-C₁₂alkynylthio, C₃-C₁₂alkynylsulfinyl, C₃-C₁₂alkynylsulfonyl,     C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio,     C₁-C₄alkoxycarbonyl-C₁-C₄alkyl-sulfinyl,     C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O,     C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₃₇R₃₈N,     R₃₉R₄₀NNH, R₄₁R₄₂NC(O)O—, R₄₃R₄₄NC(O)N H—, C, —C₁₋₈alkylcarbonyloxy,     C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy,     C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy,     C₁-C₁₂alkylthiocarbonyloxy or C₁-C₁₂alkylthiocarbamoyl, wherein the     alkyl, alkenyl and alkynyl groups may be substituted by halogen,     C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl     or by cyano; or R₃₆ is phenoxy, phenylthio, phenylsulfinyl,     phenylsulfonyl, phenylsulfonylamino, phenyl-sulfonyloxy or     benzoyloxy, wherein the phenyl groups may in turn be substituted one     or more times by halogen, nitro, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl,     C₁-C₄alkoxy or by C₁-C₄halo-alkoxy, -   or R₃₆ is a group Het₇-thio, Het₈-sulfinyl, Het₉-sulfonyl,     Het₁₀-(CO)O or Het₁₁-N(R₄₇); wherein Het₇, Het₈, Het₉, Het₁₀ and     Het₁₁ are each independently of the others a five- to ten-membered,     monocyclic or fused bicyclic ring system, which may be aromatic or     partially saturated and which may contain from 1 to 4 hetero atoms     selected from nitrogen, oxygen and sulfur and wherein each ring     system may contain no more than two oxygen atoms and no more than     two sulfur atoms and the ring system may itself be substituted by     C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,     C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkyl-sulfonyl,     di(C₁-C₄alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano,     nitro or by phenyl, and wherein the substituents on the nitrogen in     the heterocyclic ring are other than halogen; R₃₇, R₃₈, R₃₉, R₄₀,     R₄₁, R₄₂, R₄₃, R₄₄ and R₄₇ are each independently of the others     hydrogen or C₁-C₆alkyl; or -   R₃₇ and R₃₈ together or R₃₉ and R₄₀ together or R₄₁ and R₄₂ together     or R₄₃ and R₄₄ together are pyrrolidino, piperidino, morpholino or     thiomorpholino, each of which may be mono- or poly-substituted by     methyl groups; -   or Q is Q₃     wherein -   R₄₉ is C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl or     halo-substituted C₃-C₆cycloalkyl; -   R₅₀ is C₁-C₃alkylene, which may be substituted by halogen, hydroxy,     C₁-C₆alkoxy, C₂-C₆-alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl,     C₁-C₆alkoxy-C₁-C₆alkoxy, C₁-C₆alkoxy-C₁-C₆alkoxy-C₁-C₆alkoxy,     (3-oxetanyl)-oxy, or by (3-oxetanyl)-oxy substituted by C₁-C₆alkyl,     or by benzylthio, benzylsulfinyl, benzylsulfonyl, phenyl, phenoxy,     phenylthio, phenylsulfinyl or by phenylsulfonyl, wherein the phenyl-     and benzyl-containing groups may in turn be substituted by one or     more C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,     halogen, cyano, hydroxy or nitro groups; -   or R₅₀ is phenyl, wherein the phenyl-containing group may in turn be     substituted by one or more C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,     C₁-C₆haloalkoxy, halogen, cyano, hydroxy or nitro substituents, -   or R₅₀ is C₃-C₆cycloalkyl, C₃-C₆cycloalkyl substituted by     C₁-C₆alkoxy or by C₁-C₆alkyl, 3-oxetanyl or 3-oxetanyl substituted     by C₁-C₆alkyl; and -   n is 0, 1 or 2; or of an agronomically acceptable     salt/N-oxide/isomer/enantiomer of such a compound except for the     compound     4-hydroxy-3-[2-(2-methoxyethoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonyl]-bicyclo[3.2.1]oct-3-en-2-one,     and with the provisos that —R₁—X₁—R₂ is other than     C₁-C₄alkoxy-C₁-C₄alkoxy-C₁-C₄alkyl when -   a) Q is Q₁ wherein A₁ is C(R₁₄R₁₅) and A₂ is C(R₁₇R₁₈), R₁₅, R₁₇ and     R₁₈ are hydrogen and R₁₄ and R₂₂ together form a C₂-C₃alkylene     chain; and when -   b) Q is Q₁, R₁₄ and R₂₂ do not together form a C₂-C₃alkylene chain,     A₁ is C(R₁₄R₁₅), or A₁ is NR₁₆ and A₂ is oxygen; and when -   c) Q is Q₃, -   and -   b) a synergistically effective amount of one or more compounds     selected from a compound of formula 2.1     wherein R₅₁ is CH₂—OMe, ethyl or hydrogen; -   R₅₂ is hydrogen, or R₅₁ and R₅₂ together are the group     —CH═CH—CH═CH—; and a compound of formula 2.2     wherein R₅₃ is ethyl, R₅₄ is methyl or ethyl, and R₅₅ is     —CH(Me)—CH₂OMe, <S>—CH(Me)—CH₂OMe, CH₂OMe or CH₂O—CH₂CH₃; and a     compound of formula 2.3     wherein R₅₆ is CH(Me)—CH₂OMe or <S>CH(Me)—CH₂OMe; and a compound of     formula 2.4     wherein R₅₇ is chlorine, methoxy or methylthio, R₅₈ is ethyl or     isopropyl, and R₅₉ is ethyl, isopropyl, —C(CN)(CH₃)—CH₃ or     tert-butyl; -   and a compound of formula 2.5     wherein R₆₀ is ethyl or n-propyl, R₆₁ is COO⁻½ Ca⁺⁺,     —CH₂—CH(Me)S—CH₂CH₃, the group     or the group     and X is oxygen, N—O—CH₂CH₃ or N—O—CH₂CH═CH—Cl; -   and a compound of formula 2.6     wherein R₆₂ is hydrogen, methoxy or ethoxy, R₆₃ is hydrogen, methyl,     methoxy or fluorine, R₆₄ is COOMe, fluorine or chlorine, R₆₅ is     hydrogen or methyl, Y is methine, C—F or nitrogen, Z is methine or     nitrogen, and R₆₆ is fluorine or chlorine; -   and a compound of formula 2.7     wherein R₆₇ is hydrogen or —C(O)—S-n-octyl; -   and a compound of formula 2.8     wherein R₆₈ is either bromine or iodine; -   and a compound of formula 2.9     wherein R₆₉ is chlorine or nitro; -   and a compound of formula 2.10     wherein R₇₀ is fluorine or chlorine, and R₇₁ is     —CH₂—CH(Cl)—COOCH₂CH₃ or —NH—SO₂Me; -   and a compound of formula 2.11     wherein R₇₂ is trifluoromethyl or chlorine; -   and a compound of formula 2.12     wherein R₇₃ is NH₂ or <S>NH₂; -   and a compound of formula 2.13     wherein Y₂ is nitrogen, methine, C—NH—CHO, C—CH₂—NH—SO₂CH₃ or N-Me,     Y₁ is nitrogen, methine, C—Cl or C—I, Y₃ is methine, Y₄ is methine     or Y₃ and Y₄ together are sulfur or C—Cl, Y₅ is nitrogen or methine,     Y₆ is methyl, difluoromethoxy, trifluoromethyl or methoxy, Y₇ is     methoxy or difluoromethoxy and R₇₄ is CONMe₂, COOMe, COOC₂H₅,     trifluoromethyl, CH₂—CH₂CF₃, O—CH₂—CH₂C₁ or SO₂CH₂CH₃, or a sodium     salt thereof (“Me” being in each case the methyl group); -   and the compound of formula 2.13.c     and the compound of formula 2.14     and the compound of formula 2.15     and the compound of formula 2.16     and ammonium, isopropylammonium, sodium and trimesium salts thereof; -   and the compound of formula 2.17     and the compound of formula 2.18     and the compound of formula 2.19     and the compound of formula 2.20     and the compound of formula 2.21     and the compound of formula 2.22     and the compound of formula 2.23     and the compound of formula 2.24     and the compound of formula 2.25     and the compound of formula 2.26     and the compound of formula 2.27     and the compound of formula 2.28     the compound of formula 2.29     and the compound of formula 2.30     and the compound of formula 2.31     and the compound of formula 2.32     and the compound of formula 2.33     and the compound of formula 2.34     and the compound of formula 2.35     and the compound of formula 2.36     and the compound of formula 2.37     and the compound of formula 2.38     and the compound of formula 2.39     and the compound of formula 2.40     and the compound of formula 2.41     and the compound of formula 2.42     and the compound of formula 2.43     and the compound of formula 2.44     and the compound of formula 2.45     and the compound of formula 2.46     and the compound of formula 2.47     and the compound of formula 2.48     and the compound of formula 2.49     and the compound of formula 2.50     and the compound of formula 2.51     and a compound of formula 2.52     wherein -   R₀₁, R₀₂ and R₀₃ are each independently of the others halogen,     nitro, cyano, C₁-C₄alkyl, C₂-C₄alkenyl, C₂-C₄alkynyl,     C₁-C₄haloalkyl, C₂-C₆haloalkenyl, C₃-C₆cycloalkyl, halo-substituted     C₃-C₆cycloalkyl, C₁-C₆alkoxyalkyl, C₁-C₆alkylthioalkyl, hydroxy,     mercapto, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy,     C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylthio,     C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, amino, C₁-C₄alkylamino or     di(C₁-C₄alkyl)amino; -   R₀₄ and R₀₅ together are a group     —C—R₀₆(R₀₇)—O—C—R₀₈(R₀₉)—C—R₀₁₀(R₀₁₁)—C—R₀₁₂(R₀₁₃)—  (Z₁),     —C—R₀₁₄(R₀₁₅)—C—R₀₁₆(R₀₁₇)—O—C—R₀₁₈(R₀₁₉)—C—R₀₂₀(R₀₂₁)—  (Z₂) or     —C—R₀₂₂(R₀₂₃)—C—R₀₂₄(R₀₂₅)—C—R₀₂₆(R₀₂₇)—O—C—R₀₂₈(R₀₂₉)—  (Z₃),     wherein R₀₆, R₀₇, R₀₈, R₀₉, R₀₁₀, R₀₁₁, R₀₁₂, R₀₁₃, R₀₁₄, R₀₁₅,     R₀₁₆, R₀₁₇, R₀₁₈, R₀₁₉, R₀₂₀, R₀₂₁, R₀₂₂, R₀₂₃, R₀₂₄, R₀₂₅, R₀₂₆,     R₀₂₇, R₀₂₈ and R₀₂₉ are, each independently of the others, hydrogen,     halogen, C₁-C₄alkyl or C₁-C₄haloalkyl, it being possible for an     alkylene ring, which together with the carbon atoms of the group Z₁,     Z₂ or Z₃ contains from 2 to 6 carbon atoms and which may be     interrupted by oxygen, to be either fused or spiro-bound to the     carbon atoms of the group Z₁, Z₂ or Z₃ or that alkylene ring bridges     at least one ring atom of the group Z₁, Z₂ or Z₃; -   G is hydrogen, —C(X₁)—R₀₃₀, —C(X₂)—X₃—R₀₃₁, —C(X₄)—N(R₀₃₂)—R₀₃₃,     —SO₂—R₀₃₄, an alkali metal cation, alkaline earth metal cation,     sulfonium cation or ammonium cation or —P(X₅)(R₀₃₅)—R₀₃₆; X₁, X₂,     X₃, X₄ and X₅ are each independently of the others oxygen or sulfur;     and R₀₃₀, R₀₃₁, R₀₃₂, R₀₃₃, R₀₃₄, R₀₃₅ and R₀₃₆ are each     independently of the others hydrogen, C₁-C₅alkyl, C₁-C₅haloalkyl,     C₂-C₅alkenyl, C₁-C₅alkoxyalkyl, C₃-C₆cycloalkyl or phenyl, and R₀₃₄     may additionally be C₂-C₂₀alkenyl; C₂-C₂₀alkenyl substituted by     halogen, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,     C₁-C₆alkylcarbonyloxy, C₁-C₆alkoxy, C₁-C₆thioalkyl,     C₁-C₆alkylthiocarbonyl, C₁-C₆alkylcarbonylthio, C₁-C₆alkylsulfonyl,     C₁-C₆alkylsulfoxyl, C₁-C₆alkylaminosulfonyl,     C₁-C₆(di)alkylaminosulfonyl, C₁-C₆C₁-C₆ alkylsulfonyloxy,     C₁-C₆alkyl-sulfonylamino, C₁-C₆alkylamino, C₁-C₆(di)alkylamino,     C₁-C₆alkylcarbonylamino, di-C₁-C₆ alkylcarbonylamino,     C₁-C₆alkylalkylcarbonylamino, cyano, (C₃-C₇)cycloalkyl,     (C₃-C₇)heterocyclyl, tri-C₁-C₆alkylsilyl, tri-C₁-C₆alkylsilyloxy,     phenyl or heteroaryl; or R₀₃₄ is C₂-C₂₀alkynyl; C₂-C₂₀alkynyl     substituted by halogen, C₁-C₆alkylcarbonyl, C₁-C₆ alkoxycarbonyl,     C₁-C₆alkylcarbonyloxy, C₁-C₆alkoxy, C₁-C₆thioalkyl,     C₁-C₆alkylthiocarbonyl, C₁-C₆alkylcarbonylthio, C₁-C₆alkylsulfonyl,     C₁-C₆alkylsulfoxyl, C₁-C₆alkylaminosulfonyl, di-C₁-C₆     alkylaminosulfonyl, C₁-C₆alkylsulfonyloxy, C₁-C₆alkylsulfonylamino,     C₁-C₆alkylamino, di-C₁-C₆alkylamino, C₁-C₆alkylcarbonylamino,     di-C₁-C₆alkylcarbonylamino, C₁-C₆alkylcarbonylamino, cyano,     (C₃-C₇)cycloalkyl, (C₃-C₇)heterocyclyl, tri-C₁-C₆alkylsilyl,     tri-C₁-C₆alkylsilyloxy, phenyl or heteroaryl; or R₀₃₄ is     (C₁-C₇)cycloalkyl; (C₁-C₇)cycloalkyl substituted by halogen,     haloalkyl, C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylcarbonyloxy,     C₁-C₆thioalkyl, C₁-C₆alkylcarbonylthio, C₁-C₆alkylamino,     C₁-C₆alkylcarbonylamino, tri-C₁-C₆alkylsilyl or by     tri-C₁-C₆alkylsilyloxy; or R₀₃₄ is heteroaryl; heteroaryl     substituted by halogen, C₁-C₆haloalkyl, nitro, cyano, C₁-C₆alkyl,     C₁-C₆alkoxy, C₁-C₆alkylcarbonyloxy, C₁-C₆thioalkyl,     C₁-C₆alkylcarbonylthio, C₁-C₆alkylamino, C₁-C₆alkylcarbonylamino,     tri-C₁-C₆alkylsilyl or by tri-C₁-C₆alkylsilyloxy; heteroaryloxy,     heteroarylthio, heteroarylamino, di-heteroarylamino, phenylamino,     diphenylamino, C₂-C₆cycloalkylamino, di-C₂-C₆cycloalkylamino or     C₂-C₆cycloalkoxy and salts and diastereoisomers of compounds of     formula 2.52; -   and the compound of formula 2.53     and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl,     beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron,     flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl,     sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl,     flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron,     bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican,     bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben,     triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP,     mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl,     difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine,     benefin and trifluralin.

In the above formulae, “Me” is a methyl group.

The invention also includes the salts that the compounds of formula I are able to form with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases. Among the alkali metal and alkaline earth metal hydroxides used as salt formers, emphasis is to be given to the hydroxides of lithium, sodium, potassium, magnesium and calcium, but especially to those of sodium and potassium.

Examples of suitable amines for ammonium salt formation that come into consideration are ammonia as well as primary, secondary and tertiary C₁-C₁₈alkylamines, C₁-C₄hydroxyalkyl-amines and C₂-C₄alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four butylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl-ethylamine, methyl-isopropylamine, methyl-hexylamine, methyl-nonylamine, methyl-pentadecylamine, methyl-octadecylamine, ethyl-butylamine, ethyl-heptylamine, ethyl-octylamine, hexyl-heptylamine, hexyl-octylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butyl-ethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethyl-amine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butyl-amine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- and p-chloroanilines; but especially triethylamine, isopropylamine and diisopropyl-amine.

Compounds of formula I wherein p is 0 are preferred.

Preference is given to compounds of formula I wherein

-   R₁ is —CH₂—, —CH₂CH₂—, —CF₂, —CH═CHCH₂—, —CH(CH₃)— or —C≡CCH₂—, but     especially —CH₂—, in each case the left-hand free valency being     attached to the pyridine ring.

Preference is also given to those compounds of formula I wherein X₁ is oxygen, sulfonyl or a group —NR₅₂SO₂—, especially oxygen.

Of special interest are compounds of formula I wherein R₂ is —CH₂OCH₃, —CH₂OCH₂CH₃, —CH₂CH₂OCH₃, —CH₂CH₂SO₂CH₃ or —CH₂CH₂OCH₂CH₂OCH₃, preferably —CH₂CH₂OCH₃, with prominence being given to those compounds wherein X₁ is oxygen and R₁ is —CH₂—. In that group of compounds preference is given to those wherein Q is Q₁ and R₁₃ is hydroxy.

Emphasis is also given to compounds of formula I wherein R₂ is

Where no free valency is indicated in the case of those preferred meanings of R₂, for example in the case of

the attachment position is located at the carbon atom identified by “CH”.

In a further preferred group of compounds of formula I, R₃ is CF₃, CF₂CF₃, CF₂Cl, CF₂H or CCl₃, especially CF₃, R₄ preferably being hydrogen or methyl, especially hydrogen.

R₆, R₇, R₈, R₉, R₁₀, R₁₁, R₁₂, R₅₁ and R₅₂ are each independently of the others especially hydrogen, C₁-C₄alkyl, C₁-C₆alkoxy-C₁-C₆alkyl, or C₁-C₆alkoxy-C₁-C₆alkyl substituted by C₁-C₆alkoxy, while in addition, in a preferred group of compounds of formula I, Q is Q₂ and R₁ is methylene.

Very special preference is given to Q being Q₁, and R₁₃ being hydroxy or halogen, especially hydroxy. In that group of compounds, emphasis is to be given to those wherein

-   a) A₁ is C(R₁₄R₁₅) or NR₁₆, and A₂ is C(R₁₇R₁₈), C(O) or oxygen, or -   b) A₁ is C(R₁₄R₁₅) and A₂ is C(R₁₇R₁₈), and R₁₄ and R₂₂ together     form a C₂-C₃alkylene chain, preferably an ethylene chain, R₁₅, R₁₇,     R₁₈ and R₂₁ being especially hydrogen; or -   c) A₂ is C(O) or C(R₁₇R₁₈), A₁ is C(R₁₄R₁₅), and R₁₄, R₁₅, R₁₇ and     R₁₈ are each independently of the others hydrogen, methyl, ethyl,     methoxycarbonyl or ethoxycarbonyl; or -   d) R₁₄ and R₁₅ together or R₂₁ and R₂₂ together form a C₂alkylene     chain (cyclopropyl ring), A₂ is CH₂, and R₂₁ and R₂₂, or R₁₄ and     R₁₅, are each independently of the other hydrogen, C₁-C₄alkyl,     methoxycarbonyl or ethoxycarbonyl; or -   e) A₂ is C(R₁₇R₁₈) and A₁ is C(R₁₄R₁₅), and R₁₈ and R₁₄ together     form a C₂-C₃alkylene chain.

In a further group of compounds of formula I to which prominence is given, Q is Q₃, R₄₉ is cyclopropyl, and R₅₀—S(O)_(n) is methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.

Preferred synergistic mixtures according to the invention comprise as active ingredients a compound of formula I and either the compound of formula 2.2.a

aRS,1′S(-)N-(1′-methyl-2′-methoxyethyl)-N-chloroacetyl-2-ethyl-6-methylaniline), or the racemic compound of formula 2.2.b

or the compound of formula 2.2 wherein R₅₃ is ethyl, R₅₄ is methyl and R₅₅ is ethoxymethyl, or the compound of formula 2.2. wherein R₅₃ is ethyl, R₅₄ is ethyl and R₅₅ is methoxymethyl, or a compound of formula 2.3, or a compound of formula 2.30, or a compound of formula 2.4, or a compound of formula 2.13, or the compound of formula 2.14, or the compound of formula 2.6 wherein R₆₂ is hydrogen, Z is methine, R₆₃ is methyl, Y is nitrogen, R₆₄ is fluorine, R₆₅ is hydrogen and R₆₆ is fluorine or wherein R₆₂ is methoxy, Z is methine, R₆₃ is methoxy, Y is methine, R₆₄ is chlorine, R₆₅ is methyl and R₆₆ is chlorine, or the compound of formula 2.7 wherein R₆₇ is —C(O)—S-n-octyl, or a compound of formula 2.12, or the compound of formula 2.18, or the compound of formula 2.19, or the compound of formula 2.21, or the compound of formula 2.25, or the compound of formula 2.33, or the compound of formula 2.45, or a compound of formula 2.1.

Especially preferred synergistic mixtures according to the invention comprise as active ingredients a compound of formula I and either the compound of formula 2.2.a

(2.2.a, aRS,1′S(-)N-(1′-methyl-2′-methoxyethyl)-N-=chloroacetyl-2-ethyl-6-methylaniline), or the racemic compound of formula 2.2.b

or a mixture of the compounds of formulae 2.2.a and 2.2.b wherein the compound of formula 2.2.a is present in excess, preferably in a ratio by weight of from 2.5:1 to 3:1, with respect to the compound of formula 2.2.b, or the compound of formula 2.2 wherein R₅₃ is ethyl, R₅₄ is methyl and R₅₅ is ethoxymethyl, or the compound of formula 2.2 wherein R₅₃ is ethyl, R₅₄ is ethyl and R₅₅ is methoxymethyl, or a compound of formula 2.3, or the compound of formula 2.30.

Further especially preferred synergistic mixtures according to the invention comprise as active ingredients a compound of formula I and a compound of formula 2.52a as indicated in Table 1: TABLE 1 Compounds of formula 2.52a:

(2.52a) Comp. No. R₀₁ R₀₂ R₀₃ G Phys. data 1.001 CH₃ CH₃ CH₃ H m.p. 245° C. 1.002 CH₃ CH₃ CH₃ C(O)C(CH₃)₃ m.p. 135- 136° C. 1.003 CH₃ CH₃ CH₃ C(O)OCH₂CH₃ 1.004 CH₂CH₃ CH₃ CH₃ H m.p. 182- 185° C. 1.005 CH₂CH₃ CH₃ CH₃ C(O)C(CH₃)₃ m.p. 110- 113° C. 1.006 CH₂CH₃ CH₃ CH₃ C(O)OCH₂CH₃ 1.007 CH₂CH₃ CH₃ CH₂CH₃ H m.p. 189- 191° C. 1.008 CH₂CH₃ CH₃ CH₂CH₃ C(O)C(CH₃)₃ m.p. 122- 124° C. 1.009 CH₂CH₃ CH₃ CH₂CH₃ C(O)OCH₂CH₃ m.p. 114- 116° C. 1.010 CH═CH₂ CH₃ CH₃ H m.p. 165- 170° C. 1.011 CH═CH₂ CH₃ CH₃ C(O)C(CH₃)₃ m.p. 111- 113° C. 1.012 CH═CH₂ CH₃ CH₂CH₃ H 1.013 CH═CH₂ CH₃ CH═CH₂ H 1.014 CH═CH₂ CH₃ CH═CH₂ C(O)C(CH₃)₃ 1.015 C≡CH CH₃ CH₃ H m.p. 179- 184° C. 1.016 C≡CH CH₃ CH₃ C(O)C(CH₃)₃ m.p. 109- 111° C. 1.017 C≡CH CH₃ CH₃ C(O)OCH₂CH₃ 1.018 C≡CH CH₃ CH₂CH₃ H m.p. 189- 193° C. 1.019 C≡CH CH₃ CH₂CH₃ C(O)C(CH₃)₃ 1.020 O≡CH CH₃ CH₂CH₃ C(O)OCH₂CH₃ 1.021 C≡CH CH₃ C≡CH H m.p. 300° C. 1.022 C≡CH CH₃ C≡CH C(O)C(CH₃)₃ m.p. 183- 185° C. 1.023 C≡CH CH₃ C≡CH C(O)OCH₂CH₃ 1.024 C≡CH CH₃ CH═CH₂ H 1.025 C≡CCH₃ CH₃ CH₃ H m.p. 179- 181° C. 1.026 C≡CCH₃ CH₃ CH₃ C(O)C(CH₃)₃ m.p. 128- 129° C. 1.027 C≡CCH₃ CH₃ CH₃ C(O)OCH₂CH₃ 1.028 C≡CCH₃ CH₃ CH₂CH₃ H 1.029 C≡CCH₃ CH₃ CH₂CH₃ C(O)C(CH₃)₃ 1.030 C≡CCH₃ CH₃ C≡CCH₃ H 1.031 C≡CCH₃ CH₃ C≡CCH₃ C(O)C(CH₃)₃ 1.032 CH₂CH₂CH₃ CH₃ CH₃ H m.p. 136- 138° C. 1.033 CH₂CH₂CH₃ CH₃ CH₃ C(O)C(CH₃)₃ m.p. 65-  67° C. 1.034 CH₂CH₂CH₃ CH₃ CH₃ C(O)OCH₂CH₃ 1.035 CH₂CH₂CH₃ CH₃ CH₂CH₃ H 1.036 CH₂CH₂CH₃ CH₃ CH₂CH₂CH₃ H 1.037 CH₂CH₂CH₃ CH₃ CH₂CH₂CH₃ C(O)C(CH₃)₃ 1.038 CH₂CH₂CH₃ CH₃ CH₂CH₂CH₃ C(O)OCH₂CH₃ 1.039 CH₂CH₂CH₃ CH₃ C≡CH H 1.040 CH(CH₃)₂ CH₃ CH₃ H m.p. 214- 216° C. 1.041 CH(CH₃)₂ CH₃ CH₃ C(O)C(CH₃)₃ m.p. 148- 151° C. 1.042 CH(CH₃)₂ CH₃ CH₂CH₃ H 1.043 CH(CH₃)₂ CH₃ C≡CH H 1.044

CH₃ CH₃ H 1.045

CH₃ CH₂CH₃ H 1.046

CH₃ C≡CH H 1.047 CH₂CH═CH₂ CH₃ CH₃ H 1.048 CH₂CH═CH₂ CH₃ CH₂CH₃ H 1.049 CH₂CH═CH₂ CH₃ C≡CH H 1.050 CH₂CH₂CH₂CH₃ CH₃ CH₃ H 1.051 CH₂CH₂CH₂CH₃ CH₃ CH₂CH₃ H 1.052 N(CH₂CH₃)₂ CH₃ CH₃ H 1.053 N(CH₂CH₃)₂ CH₃ CH₂CH₃ H 1.054 CH₂CH CH₃ CH₃ H 1.055 CH₂OCH₃ CH₃ CH₃ H 1.056 CH₂OC(CH₃)₃ CH₃ CH₃ H 1.057 CH₃ CH₂CH₃ CH₃ H 1.058 CH₂CH₃ CH₂CH₃ CH₃ H 1.059 CH₂CH₃ CH₂CH₃ CH₂CH₃ H m.p. 185- 187° C. 1.060 CH₂CH₃ CH₂CH₃ CH₂CH₃ C(O)C(CH₃)₃ m.p. 126- 128° C. 1.061 CH₂CH₃ CH₂CH₃ CH₂CH₃ C(O)OCH₂CH₃ m.p. 105- 107° C. 1.062 CH═CH₂ CH₂CH₃ CH═CH₂ H 1.063 C≡CH CH₂CH₃ C≡CH H 1.064 CH₃ CH═CH₂ CH₃ H 1.065 CH₂CH₃ CH═CH₂ CH₂CH₃ H 1.066 CH₂CH₃ CH═CH₂ CH₃ H 1.067 CH₂CH₃ CH═CH₂ CH₃ C(O)C(CH₃)₃ m.p. 108- 110° C. 1.068 C≡CH CH═CH₂ C≡CH H 1.069 CH₃ C≡CH CH₃ H 1.070 CH₂CH₃ C≡CH CH₃ H m.p. 240- 243° C. 1.071 CH₂CH₃ C≡CH CH₃ C(O)C(CH₃)₃ m.p. 138- 140° C. 1.072 CH₂CH₃ C≡CH CH₃ C(O)OCH₂CH₃ 1.073 CH₂CH₃ C≡CH CH₂CH₃ H 1.074 CH₂CH₃ C≡CH C≡CH H 1.075 C≡CH C≡CH C≡CH H 1.076 CH₃ CH₂CH═CH₂ CH₃ H 1.077 CH₃ CH₂CH═CH₂ CH₂CH₃ H 1.078 CH₃ CH₃ Br H m.p. 234- 237° C. 1.079 CH₃ CH₃ Br C(O)C(CH₃)₃ m.p. 76-  78° C. 1.080 CH₃ CH₃ Br C(O)OCH₂CH₃ 1.081 CH₂CH₃ CH₃ Br H 1.082 C≡CH CH₃ Br H 1.083 CH₃ Br CH₃ H m.p. 298- 299° C. 1.084 CH₂CH₃ Br CH₃ H m.p. 261- 263° C. 1.085 CH₂CH₃ Br CH₃ C(O)C(CH₃)₃ m.p. 127- 130° C. 1.086 CH₂CH₃ Br CH₃ C(O)OCH₂CH₃ 1.087 CH₂CH₃ Br CH₂CH₃ H 1.088 Br CH₃ Br H m.p. 238- 241 ° C. 1.089 Br CH₃ Br C(O)C(CH₃)₃ solid 1.090 Br CH₃ Br C(O)OCH₂CH₃ 1.091 CH₃ Br Br H 1.092 CH₂CH₃ Br Br H 1.093 CH₃ CH₃ Cl H 1.094 CH₂CH₃ CH₃ Cl H 1.095 CH₃ Cl CH₃ H 1.096 CH₂CH₃ Cl CH₃ H 1.097 CH₂CH₃ Cl CH₂CH₃ H 1.098 CH₂CH₃ F CH₂CH₃ H 1.099 OH2CH₃ F C≡CH H 1.100 CH₂CH₃ F OCH₃ H 1.101 Cl CH₃ Cl H 1.102 CH₃ Cl Cl H 1.103 CH₂CH₃ Cl Cl H 1.104 Br CH₃ Cl H 1.105 CH₃ Br Cl H 1.106 CH₃ Cl Br H 1.107 CH₂CH₃ Br Cl H 1.108 CH₂CH₃ Cl Br H 1.109 OCH₃ CH₃ CH₃ H 1.110 OCH₃ CH₃ CH₂CH₃ H m.p. 178- 179° C. 1.111 OCH₃ CH₃ CH₂CH₃ C(O)C(CH₃)₃ m.p. 146- 147° C. 1.112 OCH₃ CH₃ CH₂CH₃ C(O)OCH₂CH₃ 1.113 OCH₃ CH₃ CH₂CH₂CH₃ H 1.114 OCH₃ CH₃ C≡CH H 1.115 OCH₃ CH₃ Br H 1.116 OCH₃ CH₃ OCH₃ H 1.117 C(O)CH₃ CH₃ CH₃ H solid 1.118 C(O)CH₃ CH₃ CH₂CH₃ H 1.119 CH₃ C(O)CH₃ CH₂CH₃ C(O)C(CH₃)₃ m.p. 163- 165° C. 1.120 CH₃ CH₂OH CH₂CH₃ H 1.121 CH₃ CH₃ CH₃ SO₂CH₂CHCH₂ 1.122 CH₃ CH₃ CH₃ SO₂CH₂CHCHCl 1.123 CH₃ CH₃ CH₃ SO₂CH₂CHCHCH₃ 1.124 CH₂CH₃ CH₃ CH₂CH₃ SO₂CH₂CHCH₂ 1.125 CH₂CH₃ CH₃ CH₂CH₃ SO₂CH₂CHCHCl 1.126 CH₂CH₃ CH₃ CH₂CH₃ SO₂CH₂CHCHCH₃

Combinations of the compounds of formula I with the compound of formula 2.2a

(2.2a, aRS,1′S(−)N-(1′-methyl-2′-methoxyethyl)-N-=chloroacetyl-2-ethyl-6-methylaniline) have been found to be very especially effective compositions.

The Tables that follow list especially preferred compounds of formula I for the composition according to the invention.

In the Table that follows, the left-hand valency of the radical R₁ is attached to the pyridine ring. When no free valency is indicated in the case of the substituent R₂, for example in the case of

the attachment position is located at the carbon atom identified by “CH”.

In the Table that follows, the compounds of formula I are represented as follows:

A-Q

wherein formula A

denotes the following radicals: Radical R₁ R₂ R₄ R₃ X₁ p A1 CH₂ CH₃ H CF₃ O 0 A2 CH₂ CH₃CH₂ H CF₃ O 0 A3 CH₂ (CH₂)₃CH H CF₃ O 0 A4 CH₂ PhCH₂ H CF₃ O 0 A5 CH₂ CH₃ H CF₃ S 0 A6 CH₂ CH₃ H CF₃ SO 0 A7 CH₂ CH₃ H CF₃ SO₂ 0 A8 CH₂ CH₃OCH₂ H CF₃ O 0 A9 CH₂ CH₃CH₂OCH₂ H CF₃ O 0 A10 CH₂ CH₃OCH₂CH₂ H CF₃ O 0 A11 CH₂ CH₃CH₂OCH₂CH₂ H CF₃ O 0 A12 CH₂ CH₃OC(CH₃)₂CH₂ H CF₃ O 0 A13 CH₂ CH₃OCH(CH₃)CH₂ H CF₃ O 0 A14 CH₂ CH₃OCH₂CH(CH₃) H CF₃ O 0 A15 CH₂ CH₃OCH₂C(CH₃)₂ H CF₃ O 0 A16 CH₂ CH₃OCH(CH₃) H CF₃ O 0 A17 CH₂ CH₃OC(CH₃)₂ H CF₃ O 0 A18 CH₂ HC≡CCH₂ H CF₃ O 0 A19 CH₂ H₂C═CHCH₂ H CF₃ O 0 A20 CH₂ CH₃C≡CCH₂ H CF₃ O 0 A21 CH₂

H CF₃ O 0 A22 CH₂

H CF₃ O 0 A23 CH₂

H CF₃ O 0 A24 CH₂

H CF₃ O 0 A25 CH₂

H CF₃ O 0 A26 CH₂

H CF₃ O 0 A27 CH₂

H CF₃ O 0 A28 CH₂

H CF₃ O 0 A29 CH₂

H CF₃ O 0 A30 CH₂

H CF₃ O 0 A31 CH₂

H CF₃ O 0 A32 CH₂

H CF₃ O 0 A33 CH₂

H CF₃ O 0 A34 CH₂

H CF₃ O 0 A35 CH₂

H CF₃ O 0 A36 CH₂

H CF₃ O 0 A37 CH₂

H CF₃ O 0 A38 CH₂

H CF₃ O 0 A39 CH₂

H CF₃ O 0 A40 CH₂

H CF₃ O 0 A41 CH₂

H CF₃ O 0 A42 CH₂

H CF₃ O 0 A43 CH₂

H CF₃ O 0 A44 CH₂

H CF₃ O 0 A45 CH₂

H CF₃ O 0 A46 CH₂

H CF₃ O 0 A47 CH₂

H CF₃ O 0 A48 CH₂

H CF₃ O 0 A49 CH₂

H CF₃ O 0 A50 CH₂

H CF₃ O 0 A51 CH₂

H CF₃ O 0 A52 CH₂

H CF₃ O 0 A53 CH₂

H CF₃ O 0 A54 CH₂

H CF₃ O 0 A55 CH₂

H CF₃ O 0 A56 CH₂

H CF₃ O 0 A57 CH₂

H CF₃ O 0 A58 CH₂

H CF₃ O 0 A59 CH₂

H CF₃ O 0 A60 CH₂

H CF₃ O 0 A61 CH₂

H CF₃ O 0 A62 CH₂

H CF₃ O 0 A63 CH₂

H CF₃ O 0 A64 CH₂

H CF₃ O 0 A65 CH₂

H CF₃ O 0 A66 CH₂

H CF₃ O 0 A67 CH₂

H CF₃ O 0 A68 CH₂

H CF₃ O 0 A69 CH₂

H CF₃ O 0 A70 CH₂

H CF₃ O 0 A71 CH₂

H CF₃ O 0 A72 CH₂

H CF₃ O 0 A73 CH₂

H CF₃ O 0 A74 CH₂

H CF₃ O 0 A75 CH₂

H CF₃ O 0 A76 CH₂

H CF₃ O 0 A77 CH₂

H CF₃ O 0 A78 CH₂

H CF₃ O 0 A79 CH₂

H CF₃ O 0 A80 CH₂

H CF₃ O 0 A81 CH₂

H CF₃ O 0 A82 CH₂

H CF₃ O 0 A83 CH₂

H CF₃ O 0 A84 CH₂

H CF₃ O 0 A85 CH₂

H CF₃ O 0 A86 CH₂

H CF₃ O 0 A87 CH₂

H CF₃ O 0 A88 CH₂

H CF₃ O 0 A89 CH₂

H CF₃ O 0 A90 CH₂

H CF₃ O 0 A91 CH₂CH₂ CH₃ H CF₃ O 0 A92 CH₂CH₂ CH₃CH₂ H CF₃ O 0 A93 CH₂CH₂ (CH₃)₂CH H CF₃ O 0 A94 CH₂CH₂ PhCH₂ H CF₃ O 0 A95 CH₂CH₂ CH₃ H CF₃ S 0 A96 CH₂CH₂ CH₃ H CF₃ SO 0 A97 CH₂CH₂ CH₃ H CF₃ SO₂ 0 A98 CH₂CH₂ (CH₃)₂CHCH₂ H CF₃ O A99 CH₂CH₂ CH₃OCH₂ H CF₃ O 0 A100 CH₂CH₂ CH₃CH₂OCH₂ H CF₃ O 0 A101 CH₂CH₂ CH₃OCH₂CH₂ H CF₃ O 0 A102 CH₂CH₂ CH₃CH₂OCH₂CH₂ H CF₃ O 0 A103 CH₂CH₂ CH₃OC(CH₃)₂CH₂ H CF₃ O 0 A104 CH₂CH₂ CH₃OCH(CH₃)CH₂ H CF₃ O 0 A105 CH₂CH₂ CH₃OCH₂CH(CH₃) H CF₃ O 0 A106 CH₂CH₂ CH₃OCH₂C(CH₃)₂ H CF₃ O 0 A107 CH₂CH₂ CH₃OCH(CH₃) H CF₃ O 0 A108 CH₂CH₂ CH₃OC(CH₃)₂ H CF₃ O 0 A109 CH₂CH₂ HC≡CCH₂ H CF₃ O 0 A110 CH₂CH₂ H₂C═CHCH₂ H CF₃ O 0 A111 CH₂CH₂ CH₃C≡CCH₂ H CF₃ O 0 A112 CH₂CH₂

H CF₃ O 0 A113 CH₂CH₂

H CF₃ O 0 A114 CH₂CH₂

H CF₃ O 0 A115 CH₂CH₂

H CF₃ O 0 A116 CH₂CH₂

H CF₃ O 0 A117 CH₂CH₂

H CF₃ O 0 A118 CH₂CH₂

H CF₃ O 0 A119 CH₂CH₂

H CF₃ O 0 A120 CH₂CH₂

H CF₃ O 0 A121 CH₂CH₂

H CF₃ O 0 A122 CH₂CH₂

H CF₃ O 0 A123 CH₂CH₂

H CF₃ O 0 A124 CH₂CH₂

H CF₃ O 0 A125 CH₂CH₂

H CF₃ O 0 A126 CH₂CH₂

H CF₃ O 0 A127 CH₂CH₂

H CF₃ O 0 A128 CH₂CH₂

H CF₃ O 0 A129 CH₂CH₂

H CF₃ O 0 A130 CH₂CH₂

H CF₃ O 0 A131 CH₂CH₂

H CF₃ O 0 A132 CH₂CH₂

H CF₃ O 0 A133 CH₂CH₂

H CF₃ O 0 A134 CH₂CH₂

H CF₃ O 0 A135 CH₂CH₂

H CF₃ O 0 A136 CH₂CH₂

H CF₃ O 0 A137 CH₂CH₂

H CF₃ O 0 A138 CH₂CH₂

H CF₃ O 0 A139 CH₂CH₂

H CF₃ O 0 A140 CH₂CH₂

H CF₃ O 0 A141 CH₂CH₂

H CF₃ O 0 A142 CH₂CH₂

H CF₃ O 0 A143 CH₂CH₂

H CF₃ O 0 A144 CH₂CH₂

H CF₃ O 0 A145 CH₂CH₂

H CF₃ O 0 A146 CH₂CH₂

H CF₃ O 0 A147 CH₂CH₂

H CF₃ O 0 A148 CH₂CH₂

H CF₃ O 0 A149 CH₂CH₂

H CF₃ O 0 A150 CH₂CH₂

H CF₃ O 0 A151 CH₂CH₂

H CF₃ O 0 A152 CH₂CH₂

H CF₃ O 0 A153 CH₂CH₂

H CF₃ O 0 A154 CH₂CH₂

H CF₃ O 0 A155 CH₂CH₂

H CF₃ O 0 A156 CH₂CH₂

H CF₃ O 0 A157 CH₂CH₂

H CF₃ O 0 A158 CH₂CH₂

H CF₃ O 0 A159 CH₂CH₂

H CF₃ O 0 A160 CH₂CH₂

H CF₃ O 0 A161 CH₂CH₂

H CF₃ O 0 A162 CH₂CH₂

H CF₃ O 0 A163 CH₂CH₂

H CF₃ O 0 A164 CH₂CH₂

H CF₃ O 0 A165 CH₂CH₂

H CF₃ O 0 A166 CH₂CH₂

H CF₃ O 0 A167 CH₂CH₂

H CF₃ O 0 A168 CH₂CH₂

H CF₃ O 0 A169 CH₂CH₂

H CF₃ O 0 A170 CH₂CH₂

H CF₃ O 0 A171 CH₂CH₂

H CF₃ O 0 A172 CH₂CH₂

H CF₃ O 0 A173 CH₂CH₂

H CF₃ O 0 A174 CH₂CH₂

H CF₃ O 0 A175 CH₂CH₂

H CF₃ O 0 A176 CH₂CH₂

H CF₃ O 0 A177 CH₂CH₂

H CF₃ O 0 A178 CH₂CH₂

H CF₃ O 0 A179 CH₂CH₂

H CF₃ O 0 A180 CH₂CH₂

H CF₃ O 0 A181 CH₂CH₂

H CF₃ O 0 A182 CH(OCH₃)CH₂ CH₃ H CF₃ O 0 A183 CH(OCH₃)CH₂ CH₃CH₂ H CF₃ O 0 A184 CH(OCH₃)CH₂ (CH₃)₂CH H CF₃ O 0 A185 CH(OCH₃)CH₂ PhCH₂ H CF₃ O 0 A186 CH(OCH₃)CH₂ CH₃ H CF₃ S 0 A187 CH(OCH₃)CH₂ CH₃ H CF₃ SO 0 A188 CH(OCH₃)CH₂ CH₃ H CF₃ SO₂ 0 A189 CH(OCH₃)CH₂ CH₃CH₂CH₂ H CF₃ O A190 CH(OCH₃)CH₂ CH₃OCH₂ H CF₃ O 0 A191 CH(OCH₃)CH₂ CH₃CH₂OCH₂ H CF₃ O 0 A192 CH(OCH₃)CH₂ CH₃OCH₂CH₂ H CF₃ O 0 A193 CH(OCH₃)CH₂ CH₃CH₂OCH₂CH₂ H CF₃ O 0 A194 CH(OCH₃)CH₂ CH₃OC(CH₃)₂CH₂ H CF₃ O 0 A195 CH(OCH₃)CH₂ CH₃OCH(CH₃)CH₂ H CF₃ O 0 A196 CH(OCH₃)CH₂ CH₃OCH₂CH(CH₃) H CF₃ O 0 A197 CH(OCH₃)CH₂ CH₃OCH₂C(CH₃)₂ H CF₃ O 0 A198 CH(OCH₃)CH₂ CH₃OCH(CH₃) H CF₃ O 0 A199 CH(OCH₃)CH₂ CH₃OC(CH₃)₂ H CF₃ O 0 A200 CH(OCH₃)CH₂ HC≡CCH₂ H CF₃ O 0 A201 CH(OCH₃)CH₂ H₂C═CHCH₂ H CF₃ O 0 A202 CH(OCH₃)CH₂ CH₃C≡CCH₂ H CF₃ O 0 A203 CH(OCH₃)CH₂

H CF₃ O 0 A204 CH(OCH₃)CH₂

H CF₃ O 0 A205 CH(OCH₃)CH₂

H CF₃ O 0 A206 CH(OCH₃)CH₂

H CF₃ O 0 A207 CH(OCH₃)CH₂

H CF₃ O 0 A208 CH(OCH₃)CH₂

H CF₃ O 0 A209 CH(OCH₃)CH₂

H CF₃ O 0 A210 CH(OCH₃)CH₂

H CF₃ O 0 A211 CH(OCH₃)CH₂

H CF₃ O 0 A212 CH(OCH₃)CH₂

H CF₃ O 0 A213 CH(OCH₃)CH₂

H CF₃ O 0 A214 CH(OCH₃)CH₂

H CF₃ O 0 A215 CH(OCH₃)CH₂

H CF₃ O 0 A216 CH(OCH₃)CH₂

H CF₃ O 0 A217 CH(OCH₃)CH₂

H CF₃ O 0 A218 CH(OCH₃)CH₂

H CF₃ O 0 A219 CH(OCH₃)CH₂

H CF₃ O 0 A220 CH(OCH₃)CH₂

H CF₃ O 0 A221 CH(OCH₃)CH₂

H CF₃ O 0 A222 CH(OCH₃)CH₂

H CF₃ O 0 A223 CH(OCH₃)CH₂

H CF₃ O 0 A224 CH(OCH₃)CH₂

H CF₃ O 0 A225 CH(OCH₃)CH₂

H CF₃ O 0 A226 CH(OCH₃)CH₂

H CF₃ O 0 A227 CH(OCH₃)CH₂

H CF₃ O 0 A228 CH(OCH₃)CH₂

H CF₃ O 0 A229 CH(OCH₃)CH₂

H CF₃ O 0 A230 CH(OCH₃)CH₂

H CF₃ O 0 A231 CH(OCH₃)CH₂

H CF₃ O 0 A232 CH(OCH₃)CH₂

H CF₃ O 0 A233 CH(OCH₃)CH₂

H CF₃ O 0 A234 CH(OCH₃)CH₂

H CF₃ O 0 A235 CH(OCH₃)CH₂

H CF₃ O 0 A236 CH(OCH₃)CH₂

H CF₃ O 0 A237 CH(OCH₃)CH₂

H CF₃ O 0 A238 CH(OCH₃)CH₂

H CF₃ O 0 A239 CH(OCH₃)CH₂

H CF₃ O 0 A240 CH(OCH₃)CH₂

H CF₃ O 0 A241 CH(OCH₃)CH₂

H CF₃ O 0 A242 CH(OCH₃)CH₂

H CF₃ O 0 A243 CH(OCH₃)CH₂

H CF₃ O 0 A244 CH(OCH₃)CH₂

H CF₃ O 0 A245 CH(OCH₃)CH₂

H CF₃ O 0 A246 CH(OCH₃)CH₂

H CF₃ O 0 A247 CH(OCH₃)CH₂

H CF₃ O 0 A248 CH(OCH₃)CH₂

H CF₃ O 0 A249 CH(OCH₃)CH₂

H CF₃ O 0 A250 CH(OCH₃)CH₂

H CF₃ O 0 A251 CH(OCH₃)CH₂

H CF₃ O 0 A252 CH(OCH₃)CH₂

H CF₃ O 0 A253 CH(OCH₃)CH₂

H CF₃ O 0 A254 CH(OCH₃)CH₂

H CF₃ O 0 A255 CH(OCH₃)CH₂

H CF₃ O 0 A256 CH(OCH₃)CH₂

H CF₃ O 0 A257 CH(OCH₃)CH₂

H CF₃ O 0 A258 CH(OCH₃)CH₂

H CF₃ O 0 A259 CH(OCH₃)CH₂

H CF₃ O 0 A260 CH(OCH₃)CH₂

H CF₃ O 0 A261 CH(OCH₃)CH₂

H CF₃ O 0 A262 CH(OCH₃)CH₂

H CF₃ O 0 A263 CH(OCH₃)CH₂

H CF₃ O 0 A264 CH(OCH₃)CH₂

H CF₃ O 0 A265 CH(OCH₃)CH₂

H CF₃ O 0 A266 CH(OCH₃)CH₂

H CF₃ O 0 A267 CH(OCH₃)CH₂

H CF₃ O 0 A268 CH(OCH₃)CH₂

H CF₃ O 0 A269 CH(OCH₃)CH₂

H CF₃ O 0 A270 CH(OCH₃)CH₂

H CF₃ O 0 A271 CH(OCH₃)CH₂

H CF₃ O 0 A272 CH(OCH₃)CH₂

H CF₃ O 0 A273 CH₂CH(OCH₃)CH₂ CH₃ H CF₃ O 0 A274 CH₂CH(OCH₂)CH₃ CH₂CH₃ H CF₃ O 0 A275 CH₂CH(OCH₃)CH₂ (CH₃)₂CH H CF₃ O 0 A276 CH₂CH(OCH₃)CH₂ PhCH₂ H CF₃ O 0 A277 CH₂CH(OCH₃)CH₂ CH₃ H CF₃ S 0 A278 CH₂CH(OCH₃)CH₂ CH₃ H CF₃ SO 0 A279 CH₂CH(OCH₃)CH₂ CH₃ H CF₃ SO₂ 0 A280 CH₂CH(OCH₃)CH₂ CH₃CH₂CH₂ H CF₃ O A281 CH₂CH(OCH₃)CH₂ CH₃OCH₂ H CF₃ O 0 A282 CH₂CH(OCH₃)CH₂ CH₃CH₂OCH₂ H CF₃ O 0 A283 CH₂CH(OCH₃)CH₂ CH₃OCH₂CH₂ H CF₃ O 0 A284 CH₂CH(OCH₃)CH₂ CH₃CH₂OCH₂CH₂ H CF₃ O 0 A285 CH₂CH(OCH₃)CH₂ CH₃OC(CH₃)₂CH₂ H CF₃ O 0 A286 CH₂CH(OCH₃)CH₂ CH₃OCH(CH₃)CH₂ H CF₃ O 0 A287 CH₂CH(OCH₃)CH₂ CH₃OCH₂CH(CH₃) H CF₃ O 0 A288 CH₂CH(OCH₃)CH₂ CH₃OCH₂C(CH₃)₂ H CF₃ O 0 A289 CH₂CH(OCH₃)CH₂ CH₃OCH(CH₃) H CF₃ O 0 A290 CH₂CH(OCH₃)CH₂ CH₃OC(CH₃)₂ H CF₃ O 0 A291 CH₂CH(OCH₃)CH₂ HC≡CCH₂ H CF₃ O 0 A292 CH₂CH(OCH₃)CH₂ H₂C═CHCH₂ H CF₃ O 0 A293 CH₂CH(OCH₃)CH₂ CH₃C≡CCH₂ H CF₃ O 0 A294 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A295 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A296 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A297 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A298 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A299 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A300 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A301 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A302 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A303 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A304 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A305 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A306 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A307 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A308 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A309 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A310 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A311 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A312 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A313 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A314 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A315 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A316 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A317 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A318 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A319 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A320 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A321 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A322 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A323 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A324 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A325 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A326 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A327 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A328 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A329 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A330 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A331 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A332 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A333 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A334 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A335 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A336 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A337 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A338 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A339 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A340 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A341 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A342 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A343 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A344 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A345 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A346 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A347 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A348 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A349 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A350 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A351 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A352 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A353 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A354 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A355 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A356 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A357 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A358 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A359 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A360 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A361 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A362 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A363 CH₂CH(OCH₃)CH₂

H CF₃ O 0 A364 CH═CHCH₂ CH₃ H CF₃ O 0 A365 CH═CHCH₂ CH₃CH₂ H CF₃ O 0 A366 CH═CHCH₂ (CH₃)₂CH H CF₃ O 0 A367 CH═CHCH₂ PhCH₂ H CF₃ O 0 A368 CH═CHCH₂ CH₃ H CF₃ S 0 A369 CH═CHCH₂ CH₃ H CF₃ SO 0 A370 CH═CHCH₂ CH₃ H CF₃ SO₂ 0 A371 CH═CHCH₂ CH₃CH₂CH₂ H CF₃ O A372 CH═CHCH₂ CH₃OCH₂ H CF₃ O 0 A373 CH═CHCH₂ CH₃CH₂OCH₂ H CF₃ O 0 A374 CH═CHCH₂ CH₃OCH₂CH₂ H CF₃ O 0 A375 CH═CHCH₂ CH₃CH₂OCH₂CH₂ H CF₃ O 0 A376 CH═CHCH₂ CH₃OC(CH₃)₂CH₂ H CF₃ O 0 A377 CH═CHCH₂ CH₃OCH(CH₃)CH₂ H CF₃ O 0 A378 CH═CHCH₂ CH₃OCH₂CH(CH₃) H CF₃ O 0 A379 CH═CHCH₂ CH₃OCH₂C(CH₃)₂ H CF₃ O 0 A380 CH═CHCH₂ CH₃OCH(CH₃) H CF₃ O 0 A381 CH═CHCH₂ CH₃OC(CH₃)₂ H CF₃ O 0 A382 CH═CHCH₂ HC≡CCH₂ H CF₃ O 0 A383 CH═CHCH₂ H₂C═CHCH₂ H CF₃ O 0 A384 CH═CHCH₂ CH₃C≡CCH₂ H CF₃ O 0 A385 CH═CHCH₂

H CF₃ O 0 A386 CH═CHCH₂

H CF₃ O 0 A387 CH═CHCH₂

H CF₃ O 0 A388 CH═CHCH₂

H CF₃ O 0 A389 CH═CHCH₂

H CF₃ O 0 A390 CH═CHCH₂

H CF₃ O 0 A391 CH═CHCH₂

H CF₃ O 0 A392 CH═CHCH₂

H CF₃ O 0 A393 CH═CHCH₂

H CF₃ O 0 A394 CH═CHCH₂

H CF₃ O 0 A395 CH═CHCH₂

H CF₃ O 0 A396 CH═CHCH₂

H CF₃ O 0 A397 CH═CHCH₂

H CF₃ O 0 A398 CH═CHCH₂

H CF₃ O 0 A399 CH═CHCH₂

H CF₃ O 0 A400 CH═CHCH₂

H CF₃ O 0 A401 CH═CHCH₂

H CF₃ O 0 A402 CH═CHCH₂

H CF₃ O 0 A403 CH═CHCH₂

H CF₃ O 0 A404 CH═CHCH₂

H CF₃ O 0 A405 CH═CHCH₂

H CF₃ O 0 A406 CH═CHCH₂

H CF₃ O 0 A407 CH═CHCH₂

H CF₃ O 0 A408 CH═CHCH₂

H CF₃ O 0 A409 CH═CHCH₂

H CF₃ O 0 A410 CH═CHCH₂

H CF₃ O 0 A411 CH═CHCH₂

H CF₃ O 0 A412 CH═CHCH₂

H CF₃ O 0 A413 CH═CHCH₂

H CF₃ O 0 A414 CH═CHCH₂

H CF₃ O 0 A415 CH═CHCH₂

H CF₃ O 0 A416 CH═CHCH₂

H CF₃ O 0 A417 CH═CHCH₂

H CF₃ O 0 A418 CH═CHCH₂

H CF₃ O 0 A419 CH═CHCH₂

H CF₃ O 0 A420 CH═CHCH₂

H CF₃ O 0 A421 CH═CHCH₂

H CF₃ O 0 A422 CH═CHCH₂

H CF₃ O 0 A423 CH═CHCH₂

H CF₃ O 0 A424 CH═CHCH₂

H CF₃ O 0 A425 CH═CHCH₂

H CF₃ O 0 A426 CH═CHCH₂

H CF₃ O 0 A427 CH═CHCH₂

H CF₃ O 0 A428 CH═CHCH₂

H CF₃ O 0 A429 CH═CHCH₂

H CF₃ O 0 A430 CH═CHCH₂

H CF₃ O 0 A431 CH═CHCH₂

H CF₃ O 0 A432 CH═CHCH₂

H CF₃ O 0 A433 CH═CHCH₂

H CF₃ O 0 A434 CH═CHCH₂

H CF₃ O 0 A435 CH═CHCH₂

H CF₃ O 0 A436 CH═CHCH₂

H CF₃ O 0 A437 CH═CHCH₂

H CF₃ O 0 A438 CH═CHCH₂

H CF₃ O 0 A439 CH═CHCH₂

H CF₃ O 0 A440 CH═CHCH₂

H CF₃ O 0 A441 CH═CHCH₂

H CF₃ O 0 A442 CH═CHCH₂

H CF₃ O 0 A443 CH═CHCH₂

H CF₃ O 0 A444 CH═CHCH₂

H CF₃ O 0 A445 CH═CHCH₂

H CF₃ O 0 A446 CH═CHCH₂

H CF₃ O 0 A447 CH═CHCH₂

H CF₃ O 0 A448 CH═CHCH₂

H CF₃ O 0 A449 CH═CHCH₂

H CF₃ O 0 A450 CH═CHCH₂

H CF₃ O 0 A451 CH═CHCH₂

H CF₃ O 0 A452 CH═CHCH₂

H CF₃ O 0 A453 CH═CHCH₂

H CF₃ O 0 A454 CH═CHCH₂

H CF₃ O 0 A455 C≡CCH₂ CH₃ H CF₃ O 0 A456 C≡CCH₂ CH₃CH₂ H CF₃ O 0 A457 C≡CCH₂ (CH₃)₂CH H CF₃ O 0 A458 C≡CCH₂ PhCH₂ H CF₃ O 0 A459 C≡CCH₂ CH₃ H CF₃ S 0 A460 C≡CCH₂ CH₃ H CF₃ SO 0 A461 C≡CCH₂ CH₃ H CF₃ SO₂ 0 A462 C≡CCH₂ CH₃CH₂CH₂ H CF₃ O 0 A463 C≡CCH₂ CH₃OCH₂ H CF₃ O 0 A464 C≡CCH₂ CH₃CH₂OCH₂ H CF₃ O 0 A465 C≡CCH₂ CH₃OCH₂CH₂ H CF₃ O 0 A466 C≡CCH₂ CH₃CH₂OCH₂CH₂ H CF₃ O 0 A467 C≡CCH₂ CH₃OC(CH₃)₂CH₂ H CF₃ O 0 A468 C≡CCH₂ CH₃OCH(CH₃)CH₂ H CF₃ O 0 A469 C≡CCH₂ CH₃OCH₂CH(CH₃) H CF₃ O 0 A470 C≡CCH₂ CH₃OCH₂C(CH₃)₂ H CF₃ O 0 A471 C≡CCH₂ CH₃OCH(CH₃) H CF₃ O 0 A472 C≡CCH₂ CH₃OC(CH₃)₂ H CF₃ O 0 A473 C≡CCH₂ HC≡CCH₂ H CF₃ O 0 A474 C≡CCH₂ H₂C═CHCH₂ H CF₃ O 0 A475 C≡CCH₂ CH₃C≡CCH₂ H CF₃ O 0 A476 C≡CCH₂

H CF₃ O 0 A477 C≡CCH₂

H CF₃ O 0 A478 C≡CCH₂

H CF₃ O 0 A479 C≡CCH₂

H CF₃ O 0 A480 C≡CCH₂

H CF₃ O 0 A481 C≡CCH₂

H CF₃ O 0 A482 C≡CCH₂

H CF₃ O 0 A483 C≡CCH₂

H CF₃ O 0 A484 C≡CCH₂

H CF₃ O 0 A485 C≡CCH₂

H CF₃ O 0 A486 C≡CCH₂

H CF₃ O 0 A487 C≡CCH₂

H CF₃ O 0 A488 C≡CCH₂

H CF₃ O 0 A489 C≡CCH₂

H CF₃ O 0 A490 C≡CCH₂

H CF₃ O 0 A491 C≡CCH₂

H CF₃ O 0 A492 C≡CCH₂

H CF₃ O 0 A493 C≡CCH₂

H CF₃ O 0 A494 C≡CCH₂

H CF₃ O 0 A495 C≡CCH₂

H CF₃ O 0 A496 C≡CCH₂

H CF₃ O 0 A497 C≡CCH₂

H CF₃ O 0 A498 C≡CCH₂

H CF₃ O 0 A499 C≡CCH₂

H CF₃ O 0 A500 C≡CCH₂

H CF₃ O 0 A501 C≡CCH₂

H CF₃ O 0 A502 C≡CCH₂

H CF₃ O 0 A503 C≡CCH₂

H CF₃ O 0 A504 C≡CCH₂

H CF₃ O 0 A505 C≡CCH₂

H CF₃ O 0 A506 C≡CCH₂

H CF₃ O 0 A507 C≡CCH₂

H CF₃ O 0 A508 C≡CCH₂

H CF₃ O 0 A509 C≡CCH₂

H CF₃ O 0 A510 C≡CCH₂

H CF₃ O 0 A511 C≡CCH₂

H CF₃ O 0 A512 C≡CCH₂

H CF₃ O 0 A513 C≡CCH₂

H CF₃ O 0 A514 C≡CCH₂

H CF₃ O 0 A515 C≡CCH₂

H CF₃ O 0 A516 C≡CCH₂

H CF₃ O 0 A517 C≡CCH₂

H CF₃ O 0 A518 C≡CCH₂

H CF₃ O 0 A519 C≡CCH₂

H CF₃ O 0 A520 C≡CCH₂

H CF₃ O 0 A521 C≡CCH₂

H CF₃ O 0 A522 C≡CCH₂

H CF₃ O 0 A523 C≡CCH₂

H CF₃ O 0 A524 C≡CCH₂

H CF₃ O 0 A525 C≡CCH₂

H CF₃ O 0 A526 C≡CCH₂

H CF₃ O 0 A527 C≡CCH₂

H CF₃ O 0 A528 C≡CCH₂

H CF₃ O 0 A529 C≡CCH₂

H CF₃ O 0 A530 C≡CCH₂

H CF₃ O 0 A531 C≡CCH₂

H CF₃ O 0 A532 C≡CCH₂

H CF₃ O 0 A533 C≡CCH₂

H CF₃ O 0 A534 C≡CCH₂

H CF₃ O 0 A535 C≡CCH₂

H CF₃ O 0 A536 C≡CCH₂

H CF₃ O 0 A537 C≡CCH₂

H CF₃ O 0 A538 C≡CCH₂

H CF₃ O 0 A539 C≡CCH₂

H CF₃ O 0 A540 C≡CCH₂

H CF₃ O 0 A541 C≡CCH₂

H CF₃ O 0 A542 C≡CCH₂

H CF₃ O 0 A543 C≡CCH₂

H CF₃ O 0 A544 C≡CCH₂

H CF₃ O 0 A545 C≡CCH₂

H CF₃ O 0 A546 CH₂ CH₃ H CF₂Cl O 0 A547 CH₂ CH₃CH₂ H CF₂Cl O 0 A548 CH₂ (CH₃)₂CH H CF₂Cl O 0 A549 CH₂ PhCH₂ H CF₂Cl O 0 A550 CH₂ CH₃ H CF₂Cl S 0 A551 CH₂ CH₃ H CF₂Cl SO 0 A552 CH₂ CH₃ H CF₂Cl SO₂ 0 A553 CH₂ CH₃CH₂CH₂ H CF₂Cl O 0 A554 CH₂ CH₃OCH₂ H CF₂Cl O 0 A555 CH₂ CH₃CH₂OCH₂ H CF₂Cl O 0 A556 CH₂ CH₃OCH₂CH₂ H CF₂Cl O 0 A557 CH₂ CH₃CH₂OCH₂CH₂ H CF₂Cl O 0 A558 CH₂ CH₃OC(CH₃)₂CH₂ H CF₂Cl O 0 A559 CH₂ CH₃OCH(CH₃)CH₂ H CF₂Cl O 0 A560 CH₂ CH₃OCH₂CH(CH₃) H CF₂Cl O 0 A561 CH₂ CH₃OCH₂C(CH₃)₂ H CF₂Cl O 0 A562 CH₂ CH₃OCH(CH₃) H CF₂Cl O 0 A563 CH₂ CH₃OC(CH₃)₂ H CF₂Cl O 0 A564 CH₂ HC≡CCH₂ H CF₂Cl O 0 A565 CH₂ H₂C═CHCH₂ H CF₂Cl O 0 A566 CH₂ CH₃C≡CCH₂ H CF₂Cl O 0 A567 CH₂

H CF₂Cl O 0 A568 CH₂

H CF₂Cl O 0 A569 CH₂

H CF₂Cl O 0 A570 CH₂

H CF₂Cl O 0 A571 CH₂

H CF₂Cl O 0 A572 CH₂

H CF₂Cl O 0 A573 CH₂

H CF₂Cl O 0 A574 CH₂

H CF₂Cl O 0 A575 CH₂

H CF₂Cl O 0 A576 CH₂

H CF₂Cl O 0 A577 CH₂

H CF₂Cl O 0 A578 CH₂

H CF₂Cl O 0 A579 CH₂

H CF₂Cl O 0 A580 CH₂

H CF₂Cl O 0 A581 CH₂

H CF₂Cl O 0 A582 CH₂

H CF₂Cl O 0 A583 CH₂

H CF₂Cl O 0 A584 CH₂

H CF₂Cl O 0 A585 CH₂

H CF₂Cl O 0 A586 CH₂

H CF₂Cl O 0 A587 CH₂

H CF₂Cl O 0 A588 CH₂

H CF₂Cl O 0 A589 CH₂

H CF₂Cl O 0 A590 CH₂

H CF₂Cl O 0 A591 CH₂

H CF₂Cl O 0 A592 CH₂

H CF₂Cl O 0 A593 CH₂

H CF₂Cl O 0 A594 CH₂

H CF₂Cl O 0 A595 CH₂

H CF₂Cl O 0 A596 CH₂

H CF₂Cl O 0 A597 CH₂

H CF₂Cl O 0 A598 CH₂

H CF₂Cl O 0 A599 CH₂

H CF₂Cl O 0 A600 CH₂

H CF₂Cl O 0 A601 CH₂

H CF₂Cl O 0 A602 CH₂

H CF₂Cl O 0

Radical R₁ R₂ R₄ R₃ X₁ p A603 CH₂

H CF₂Cl O 0 A604 CH₂

H CF₂Cl O 0 A605 CH₂

H CF₂Cl O 0 A606 CH₂

H CF₂Cl O 0 A607 CH₂

H CF₂Cl O 0 A608 CH₂

H CF₂Cl O 0 A609 CH₂

H CF₂Cl O 0 A610 CH₂

H CF₂Cl O 0 A611 CH₂

H CF₂Cl O 0 A612 CH₂

H CF₂Cl O 0 A613 CH₂

H CF₂Cl O 0 A614 CH₂

H CF₂Cl O 0 A615 CH₂

H CF₂Cl O 0 A616 CH₂

H CF₂Cl O 0 A617 CH₂

H CF₂Cl O 0 A618 CH₂

H CF₂Cl O 0 A619 CH₂

H CF₂Cl O 0 A620 CH₂

H CF₂Cl O 0 A621 CH₂

H CF₂Cl O 0 A622 CH₂

H CF₂Cl O 0 A623 CH₂

H CF₂Cl O 0 A624 CH₂

H CF₂Cl O 0 A625 CH₂

H CF₂Cl O 0 A626 CH₂

H CF₂Cl O 0 A627 CH₂

H CF₂Cl O 0 A628 CH₂

H CF₂Cl O 0 A629 CH₂

H CF₂Cl O 0 A630 CH₂

H CF₂Cl O 0 A631 CH₂

H CF₂Cl O 0 A632 CH₂

H CF₂Cl O 0 A633 CH₂

H CF₂Cl O 0 A634 CH₂

H CF₂Cl O 0 A635 CH₂

H CF₂Cl O 0 A636 CH₂

H CF₂Cl O 0 A637 CH₂ CH₃ H CHF₂ O 0 A638 CH₂ CH₂CH₃ H CHF₂ O 0 A639 CH₂ (CH₃)₂CH H CHF₂ O 0 A640 CH₂ PhCH₂ H CHF₂ O 0 A641 CH₂ CH₃ H CHF₂ O 0 A642 CH₂ CH₃ H CHF₂ O 0 A643 CH₂ CH₃ H CHF₂ O 0 A644 CH₂ CH₃OCH₂ H CHF₂ O 0 A645 CH₂ CH₃CH₂OCH₂ H CHF₂ O 0 A646 CH₂ CH₃OCH₂CH₂ H CHF₂ O 0 A647 CH₂ CH₃CH₂OCH₂CH₂ H CHF₂ O 0 A648 CH₂ CH₃OC(CH₃)₂CH₂ H CHF₂ O 0 A649 CH₂ CH₃OCH(CH₃)CH₂ H CHF₂ O 0 A650 CH₂ CH₃OCH₂CH(CH₃) H CHF₂ O 0 A651 CH₂ CH₃OCH₂C(CH₃)₂ H CHF₂ O 0 A652 CH₂ CH₃OCH(CH₃) H CHF₂ O 0 A653 CH₂ CH₃OC(CH₃)₂ H CHF₂ O 0 A654 CH₂ HC≡CCH₂ H CHF₂ O 0 A655 CH₂ H₃C═CHCH₂ H CHF₂ O 0 A656 CH₂ CH₃C≡CCH₂ H CHF₂ O 0 A657 CH₂

H CHF₂ O 0 A658 CH₂

H CHF₂ O 0 A659 CH₂

H CHF₂ O 0 A660 CH₂

H CHF₂ O 0 A661 CH₂

H CHF₂ O 0 A662 CH₂

H CHF₂ O 0 A663 CH₂

H CHF₂ O 0 A664 CH₂

H CHF₂ O 0 A665 CH₂

H CHF₂ O 0 A666 CH₂

H CHF₂ O 0 A667 CH₂

H CHF₂ O 0 A668 CH₂

H CHF₂ O 0 A669 CH₂

H CHF₂ O 0 A670 CH₂

H CHF₂ O 0 A671 CH₂

H CHF₂ O 0 A672 CH₂

H CHF₂ O 0 A673 CH₂

H CHF₂ O 0 A674 CH₂

H CHF₂ O 0 A675 CH₂

H CHF₂ O 0 A676 CH₂

H CHF₂ O 0 A677 CH₂

H CHF₂ O 0 A678 CH₂

H CHF₂ O 0 A679 CH₂

H CHF₂ O 0 A680 CH₂

H CHF₂ O 0 A681 CH₂

H CHF₂ O 0 A682 CH₂

H CHF₂ S 0 A683 CH₂

H CHF₂ SO 0 A684 CH₂

H CHF₂ SO₂ 0 A685 CH₂

H CHF₂ O 0 A686 CH₂

H CHF₂ O 0 A687 CH₂

H CHF₂ O 0 A688 CH₂

H CHF₂ O 0 A689 CH₂

H CHF₂ O 0 A690 CH₂

H CHF₂ O 0 A691 CH₂

H CHF₂ O 0 A692 CH₂

H CHF₂ O 0 A693 CH₂

H CHF₂ O 0 A694 CH₂

H CHF₂ O 0 A695 CH₂

H CHF₂ O 0 A696 CH₂

H CHF₂ O 0 A697 CH₂

H CHF₂ O 0 A698 CH₂

H CHF₂ O 0 A699 CH₂

H CHF₂ O 0 A700 CH₂

H CHF₂ O 0 A701 CH₂

H CHF₂ O 0 A702 CH₂

H CHF₂ O 0 A703 CH₂

H CHF₂ O 0 A704 CH₂

H CHF₂ O 0 A705 CH₂

H CHF₂ O 0 A706 CH₂

H CHF₂ O 0 A707 CH₂

H CHF₂ O 0 A708 CH₂

H CHF₂ O 0 A709 CH₂

H CHF₂ O 0 A710 CH₂

H CHF₂ O 0 A711 CH₂

H CHF₂ O 0 A712 CH₂

H CHF₂ O 0 A713 CH₂

H CHF₂ O 0 A714 CH₂

H CHF₂ O 0 A715 CH₂

H CHF₂ O 0 A716 CH₂

H CHF₂ O 0 A717 CH₂

H CHF₂ O 0 A718 CH₂

H CHF₂ O 0 A719 CH₂

H CHF₂ O 0 A720 CH₂

H CHF₂ O 0 A721 CH₂

H CHF₂ O 0 A722 CH₂

H CHF₂ O 0 A723 CH₂

H CHF₂ O 0 A724 CH₂

H CHF₂ O 0 A725 CH₂

H CHF₂ O 0 A726 CH₂

H CHF₂ O 0 A727 CH₂ CH₃ H CF₃ O 1 A728 CH₂ CH₂CH₃ H CF₃ O 1 A729 CH₂ (CH₃)₂CH H CF₃ O 1 A730 CH₂ PhCH₂ H CF₃ O 1 A731 CH₂ CH₃ H CF₃ S 1 A732 CH₂ CH₃ H CF₃ SO 1 A733 CH₂ CH₃ H CF₃ SO₂ 1 A734 CH₂ CH₃OCH₂ H CF₃ O 1 A735 CH₂ CH₃CH₂OCH₂ H CF₃ O 1 A736 CH₂ CH₃OCH₂CH₂ H CF₃ O 1 A737 CH₂ CH₃CH₂OCH₂CH₂ H CF₃ O 1 A738 CH₂ CH₃OC(CH₃)₂CH₂ H CF₃ O 1 A739 CH₂ CH₃OCH(CH₃)CH₂ H CF₃ O 1 A740 CH₂ CH₃OCH₂CH(CH₃) H CF₃ O 1 A741 CH₂ CH₃OCH₂C(CH₃)₂ H CF₃ O 1 A742 CH₂ CH₃OCH(CH₃) H CF₃ O 1 A743 CH₂ CH₃OC(CH₃)₂ H CF₃ O 1 A744 CH₂ HC≡CCH₂ H CF₃ O 1 A745 CH₂ H₃C═CHCH₂ H CF₃ O 1 A746 CH₂ CH₃C≡CCH₂ H CF₃ O 1 A747 CH₂

H CF₃ O 1 A748 CH₂

H CF₃ O 1 A749 CH₂

H CF₃ O 1 A750 CH₂

H CF₃ O 1 A751 CH₂

H CF₃ O 1 A752 CH₂

H CF₃ O 1 A753 CH₂

H CF₃ O 1 A754 CH₂

H CF₃ O 1 A755 CH₂

H CF₃ O 1 A756 CH₂

H CF₃ O 1 A757 CH₂

H CF₃ O 1 A758 CH₂

H CF₃ O 1 A759 CH₂

H CF₃ O 1 A760 CH₂

H CF₃ O 1 A761 CH₂

H CF₃ O 1 A762 CH₂

H CF₃ O 1 A763 CH₂

H CF₃ O 1 A764 CH₂

H CF₃ O 1 A765 CH₂

H CF₃ O 1 A766 CH₂

H CF₃ O 1 A767 CH₂

H CF₃ O 1 A768 CH₂

H CF₃ O 1 A769 CH₂

H CF₃ O 1 A770 CH₂

H CF₃ O 1 A771 CH₂

H CF₃ O 1 A772 CH₂

H CF₃ O 1 A773 CH₂

H CF₃ O 1 A774 CH₂

H CF₃ O 1 A775 CH₂

H CF₃ O 1 A776 CH₂

H CF₃ O 1 A777 CH₂

H CF₃ O 1 A778 CH₂

H CF₃ O 1 A779 CH₂

H CF₃ O 1 A780 CH₂

H CF₃ O 1 A781 CH₂

H CF₃ O 1 A782 CH₂

H CF₃ O 1 A783 CH₂

H CF₃ O 1 A784 CH₂

H CF₃ O 1 A785 CH₂

H CF₃ O 1 A786 CH₂

H CF₃ O 1 A787 CH₂

H CF₃ O 1 A788 CH₂

H CF₃ O 1 A789 CH₂

H CF₃ O 1 A790 CH₂

H CF₃ O 1 A791 CH₂

H CF₃ O 1 A792 CH₂

H CF₃ O 1 A793 CH₂

H CF₃ O 1 A794 CH₂

H CF₃ O 1 A795 CH₂

H CF₃ O 1 A796 CH₂

H CF₃ O 1 A797 CH₂

H CF₃ O 1 A798 CH₂

H CF₃ O 1 A799 CH₂

H CF₃ O 1 A800 CH₂

H CF₃ O 1 A801 CH₂

H CF₃ O 1 A802 CH₂

H CF₃ O 1 A803 CH₂

H CF₃ O 1 A804 CH₂

H CF₃ O 1 A805 CH₂

H CF₃ O 1 A806 CH₂

H CF₃ O 1 A807 CH₂

H CF₃ O 1 A808 CH₂

H CF₃ O 1 A809 CH₂

H CF₃ O 1 A810 CH₂

H CF₃ O 1 A811 CH₂

H CF₃ O 1 A812 CH₂

H CF₃ O 1 A813 CH₂

H CF₃ O 1 A814 CH₂

H CF₃ O 1 A815 CH₂

H CF₃ O 1 A816 CH₂

H CF₃ O 1 A817 CH₂ CH₃SCH₂CH₂ H CF₃ O 0 A818 CH₂ CH₃SOCH₂CH₂ H CF₃ O 0 A819 CH₂ CH₃SO₂CH₂CH₂ H CF₃ O 0 A820 CH₂ CH₃OCH₂CH₂ H CF₂Cl O 1 A821 CH₂ CH₃OCH₂CH₂ H CF₂H O 1 A822 CH₂ CH₃OCH₂CH₂ F CF₃ O 0 A823 CH₂ CH₃OCH₂CH₂ CH₃ CF₃ O 0 A824 CH₂ CH₃OCH₂CH₂ CH₃ CF₃ O 1 A825 CH₂ CH₃OCH₂CH₂ H CF₃ S 0 A826 CH₂ CH₃OCH₂CH₂ H CF₃ SO 0 A827 CH₂ CH₃OCH₂CH₂ CH₃ CF₃ SO₂ 0 A828 CH₂ CH₃SO₂CH₂CH₂ CH₃ CF₃ O 0 A829 CH₂

H CF₃ S 0 A830 CH₂

H CF₃ S 0 A831 CH₂

CH₃ CF₃ S 0 A832 CH₂

CH₃ CF₃ S 0 A833 CH₂ CH₃C(O) H CF₃ O 0 A834 CH₂ CF₃CH₂ H CF₃ O 0 A835 CH₂ CH₃OCH₂CH₂OCH₂CH₂ H CF₃ O 0 A836 CH₂ HC≡CCH₂CH₂ H CF₃ O 0 A837 CH₂

H CF₃ O 0 A838 CH₂ CH₃CH₂C(OCH₃)HOCH₂CH₂ H CF₃ O 0 A839 CH₂ (CH₃)₃CC(O) H CF₃ O 0 A840 CH₂ CH₂═CHCH₂OCH₂CH₂ H CF₃ O 0 A841 CH₂ CH₃CH₂CH₂OCH₂CH₂ H CF₃ O 0 A842 CH₂

H CF₃ O 0 A843 CH₂ n-heptyl-C(O) H CF₃ O 0 A844 CH₂ phenyl-C(O) H CF₃ O 0 A845 CH₂ CF₃CH₂OCH₂CH₂ H CF₃ O 0 A846 CH₂ CH₃OCH₂CH₂CH₂ H CF₃ O 0 A847 CH₂ HOCH₂CH₂CH₂ H CF₃ O 0 A848 CH₂

H CF₃ O 0 A849 CH₂ N≡CCH₂CH₂ H CF₃ O 0 A850 CH₂ ClCH₂CH₂ H CF₃ O 0 A851 CH₂

H CF₃ O 0 A852 CH₂

H CF₃ O 0 A853 CH₂ CH₃OCH₂C(Br)HCH₂ H CF₃ O 0 A854 CH₂

H CF₃ O 0 A855 CH₂

H CF₃ O 0 A856 CH₂ HOCH₂CH₂ H CF₃ O 0 A857 CH₂

H CF₃ O 0 A858 CH₂ CH₃(OCH₂CH₂)₃ H CF₃ O 0 A859 CH₂ CH₃CH₂OC(CH₃)HOCH₂CH₂ H CF₃ O 0 A860 CH₂ n-heptyl-C(O)OCH₂CH₂ H CF₃ O 0 A861 CH₂ CH₃C(O)OCH₂CH₂ H CF₃ O 0 A862 CH₂ CH₃SO₂OCH₂CH₂ H CF₃ O 0 A863 CH₂

H CF₃ O 0 A864 CH₂ CH₃ H CF₃ —NCH₃SO₂— 0 A865 CH₂ HOCH₂C(OH)HCH₂ H CF₃ O 0 A866 CH₂ phenyl-C(O)OCH₂CH₂ H CF₃ O 0 A867 CH₂ tert-butyl-C(O)OCH₂CH₂ H CF₃ O 0 A868 CH₂ CH₃OC(O)CH₂ H CF₃ O 0

In the Table that follows, when the substituents A₁ and A₂ are rings the ring attachment positions are at the carbon atom identified by “C”, for example

in the case of open-chain structures, “(CH₃)₂C”, for example, is

Q in the formula A-Q denotes Q₁

and Q₁ denotes the following radicals B: Radical A₁ A₂ n R₂₁ R₂₂ R₁₃ B1 CH₂ CH₂ 0 H H OH B2 CH₂ CH₂ 0 CH₃ H OH B3 CH₂ CH₂ 0 CH₃ CH₃ OH B4 (CH₃)CH CH₂ 0 CH₃ CH₃ OH B5 (CH₂)₂C CH₂ 0 CH₃ CH₃ OH B6 CH CH 0 CH₃ — OH B7 CH₂ CH₂ 0 CH₃ CH₂═CHCH₂ OH B8 CH₂ CH₂ 0 CH₃ HC≡CCH₂ OH B9 CH₂ CH₂ 0 CH₃ CH₃S OH B10 CH₂ CH₂ 0 CH₃ CH₃SO OH B11 CH₂ CH₂ 0 CH₃ CH₃SO₂ OH B12 CH₂ CH₂ 0 CH₃ CH₃O OH B13 CH₂ CH₂ 0 CH₃ CH₃OC(O) OH B14 CH₂ CH₂ 0 CH₃ CH₃CH₂OC(O) OH B15 CH₂ (CH₃)₂C 0 H H OH B16

CH₂ 0 H H OH B17

CH₂ 0 H H OH B18

CH₂ 0 CH₃ H OH B19

CH₂ 0 CH₃ CH₃ OH B20

CH₂ 0 H H OH B21

CH₂ 0 CH₃ H OH B22

CH₂ 0 CH₃ CH₃ OH B23 (CH₃)₂C O 0 CH₃ CH₃ OH B24 CH₂ O 0 CH₃ CH₃ OH B25 CH₃N O 0 CH₃ CH₃ OH B26

O 0 CH₃ CH₃ OH B27 CH₃N CH₂ 0 CH₃ CH₃ OH B28 CH₃N (CH₃CH 0 H H OH B29 CH₃N (CH₃CH 0 CH₃ H OH B30 NH (CH₃C 0 H — OH B31 NH CH 0 CH₃ — OH B32 CH₃N (CH₃C 0 H — OH B33 CH₃N CH 0 CH₃ — OH B34 O (CH₃)₂C 0 H — OH B35 O (CH₃)₂C 0 CH₃ CH₃ OH B36 O (CH₃)₂C 0 CH₃ H OH B37 O (CH₃)₂C 0 H — OH B38 O CH 0 CH₃ — OH B39 (CH₃)₂C C═O 0 CH₃ CH₃ OH B40 (CH₃)₂C (OH)CH 0 CH₃ CH₃ OH B41

C═O 0 CH₃ CH₃ OH B42

C═O 0 CH₂ CH₂ OH B43 (CH₃)₂C

0 CH₃ CH₃ OH B44 (CH₃)₂C

0 CH₃ CH₃ OH B45 (CH₃)₂C

0 CH₃ CH₃ OH B46 (CH₃)₂C

0 CH₃ CH₃ OH B47 (CH₃)₂C HON═C 0 CH₃ CH₃ OH B48 (CH₃)₂C CH₃ON═C 0 CH₃ CH₃ OH B49 (CH₃)₂C BnON═C 0 CH₃ CH₃ OH B50 CH O 1 H CH₂ OH B51 CH C═O 1 H CH₂ OH B52 CH CH₂ 1 H CH₂ OH B53 CH CH₃N 1 H CH₂ OH B54 CH CH₂CH₂ 1 H CH₂ OH B55 CH C═O 2 H CH₂ OH B56 CH CH₂ 2 H CH₂ OH B57 CH CH₂ 1 H CH₂ Cl B58 CH CH₂ 1 H CH₂ NH₂ B59 CH CH₂ 1 H CH₂ CH₃SO₂NH B60 CH CH₂ 1 H CH₂ CH₃OCH₂CH₂S B61 CH CH₂ 1 H CH₂ CH₃OCH₂CH₂SO B62 CH CH₂ 1 H CH₂ CH₃OCH₂CH₂SO₂ B63 CH CH₂ 1 H CH₂ (CH₃)₂NC(O)NH B64 CH CH₂ 1 H CH₂ PhC(O)O B65 CH CH₂ 1 H CH₂ CH₃OC(O)O B66 CH CH₂ 1 H CH₂ CH₃(CH₂)₇S B67 CH CH₂ 1 H CH₂ CH₃(CH₂)₇SO B68 CH CH₂ 1 H CH₂ CH₃(CH₂)₇SO₂ B69 CH CH₂ 1 H CH₂ (CH₃)₂NSO₂NH B70 CH CH₂ 1 H CH₂ PhS B71 CH CH₂ 1 H CH₂ PhSO B72 CH CH₂ 1 H CH₂ PhSO₂ B73 CH CH₂ 1 H CH₂

B74 CH CH₂ 1 H CH₂

B75 (CH₃)₂C C═O 0 CH₃ CH₃ Cl B76 (CH₃)₂C C═O 0 CH₃ CH₃ NH₂ B77 (CH₃)₂C C═O 0 CH₃ CH₃ CH₃SO₂NH B78 (CH₃)₂C C═O 0 CH₃ CH₃ CH₃OCH₂CH₂S B79 (CH₃)₂C C═O 0 CH₃ CH₃ CH₃OCH₂CH₂SO B80 (CH₃)₂C C═O 0 CH₃ CH₃ CH₃OCH₂CH₂SO₂ B81 (CH₃)₂C C═O 0 CH₃ CH₃ (CH₃)₂NC(O)NH B82 (CH₃)₂C C═O 0 CH₃ CH₃ PhC(O)O B83 (CH₃)₂C C═O 0 CH₃ CH₃ CH₃OC(O)O B84 (CH₃)₂C C═O 0 CH₃ CH₃ CH₃(CH₂)₇S B85 (CH₃)₂C C═O 0 CH₃ CH₃ CH₃(CH₂)₇SO B86 (CH₃)₂C C═O 0 CH₃ CH₃ CH₃(CH₂)₇SO₂ B87 (CH₃)₂C C═O 0 CH₃ CH₃ (CH₃)₂NSO₂NH B88 (CH₃)₂C C═O 0 CH₃ CH₃ PhS B89 (CH₃)₂C C═O 0 CH₃ CH₃ PhSO B90 (CH₃)₂C C═O 0 CH₃ CH₃ PhSO₂ B91 (CH₃)₂C C═O 0 CH₃ CH₃

B92 (CH₃)₂C C═O 0 CH₃ CH₃

B93 (CH₃)₂C CH₂ 0 H H Cl B94 (CH₃)₂C CH₂ 0 H H NH₂ B96 (CH₃)₂C CH₂ 0 H H CH₃OCH₂CH₂S B97 (CH₃)₂C CH₂ 0 H H CH₃OCH₂CH₂SO B98 (CH₃)₂C CH₂ 0 H H CH₃OCH₂CH₂SO₂ B99 (CH₃)₂C CH₂ 0 H H (CH₃)₂NC(O)NH B100 (CH₃)₂C CH₂ 0 H H PhC(O)O B101 (CH₃)₂C CH₂ 0 H H CH₃OC(O)O B102 (CH₃)₂C CH₂ 0 H H CH₃(CH₂)₇S B103 (CH₃)₂C CH₂ 0 H H CH₃(CH₂)₇SO B104 (CH₃)₂C CH₂ 0 H H CH₃(CH₂)₇SO₂ B105 (CH₃)₂C CH₂ 0 H H (CH₃)₂NSO₂NH B106 (CH₃)₂C CH₂ 0 H H PhS B107 (CH₃)₂C CH₂ 0 H H PhSO B108 (CH₃)₂C CH₂ 0 H H PhSO₂ B109 (CH₃)₂C CH₂ 0 H H

B110 (CH₃)₂C CH₂ 0 H H

B111 CH₂ (CH₃)CH 0 H H OH B112 CH₂ CH₂ 1 H CH₂ tert-butyl-C(O)O B113 CH₂ CH₂ 1 H CH₂ tert-heptyl-C(O)O or Q in the formula A-Q denotes Q₂

and Q₂ denotes the following radicals C: Radical R₃₄ R₃₅ R₃₆ C1 CH₃ H OH C2 CH₃ CH₃ OH C3 H HC≡CCH₂ OH C4 H CH₃SO₂ OH C5 H CH₃ OH C6 H PhCH₂ OH C7 CF₃ CH₃ OH C8

CH₃ OH C9 CH₃OCH₂CH₂OCH₂ CH₃ OH C10 H CH₃ Cl C11 H CH₃ NH₂ C12 H CH₃ CH₃SO₂NH C13 H CH₃ CH₃OCH₂CH₂S C14 H CH₃ CH₃OCH₂CH₂SO C15 H CH₃ CH₃OCH₂CH₂SO₂ C16 H CH₃ (CH₃)₂NC(O)NH C17 H CH₃ PhC(O)O C18 H CH₃ CH₃OC(O)O C19 H CH₃ CH₃(CH₂)₇S C20 H CH₃ CH₃(CH₂)₇SO C21 H CH₃ CH₃(CH₂)₇SO₂ C22 H CH₃ (CH₃)₂NSO₂NH C23 H CH₃ PhS C24 H CH₃ PhSO C25 H CH₃ PhSO₂ C26 H CH₃

C27 H CH₃

C28 H CH₃ CH₃SO₂O C29 H CH₃ p-tolylSO₂O or Q in the formula A-Q denotes Q₃

and Q₃ denotes the following radicals D (attachment position of R₄₉ to the heterocycle is the group “CH”): Radical R₄₉ R₅₀ n D1

CH₃ 0 D2

CH₃ 1 D3

CH₃ 2 D4

CF₃ 0 D5

CF₃ 1 D6

CF₃ 2 D7

Ph 0 D8

Ph 1 D9

Ph 2 D10

PhCH₂ 0 D11

PhCH₂ 1 D12

PhCH₂ 2

TABLE 2 Compounds of formula I, represented as compounds of formula A-Q wherein Q is Q₁, and Q₁ is the radical B52: B52 B52 B52 B52 B52 B52 B52 B52 B52 B52 B52 B52 A1 A2 A3 A4 A5 A6 A7 A18 A19 A20 A21 A22 A23 A24 A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36 A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48 A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60 A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A71 A72 A73 A74 A75 A76 A77 A78 A79 A80 A81 A82 A83 A84 A85 A86 A87 A88 A89 A90 A91 A92 A93 A94 A95 A96 A97 A98 A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120 A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132 A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144 A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156 A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168 A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180 A181 A182 A183 A184 A185 A186 A187 A188 A189 A200 A201 A202 A203 A204 A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216 A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228 A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240 A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252 A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264 A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276 A277 A278 A279 A280 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300 A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312 A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324 A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336 A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348 A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360 A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A382 A383 A384 A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396 A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408 A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420 A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432 A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444 A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456 A457 A458 A459 A460 A461 A462 A473 A474 A475 A476 A477 A478 A479 A480 A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492 A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504 A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516 A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528 A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540 A541 A542 A543 A544 A545 A546 A547 A548 A549 A550 A551 A552 A553 A564 A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576 A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588 A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600 A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612 A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624 A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636 A637 A638 A639 A640 A641 A642 A643 A654 A655 A656 A657 A658 A659 A660 A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672 A673 A674 A675 A676 A677 A678 A679 A680 A681 A682 A683 A684 A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696 A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708 A709 A710 A711 A712 A713 A714 A715 A716 A717 A718 A719 A720 A721 A722 A723 A724 A725 A726 A727 A728 A729 A730 A731 A732 A733 A744 A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756 A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768 A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780 A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792 A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804 A805 A806 A807 A808 A809 A810 A811 A812 A813 A814 A815 A816 A817 A818 A819 A820 A821 A822 A823 A824 A825 A826 A827 A828 A829 A830 A831 A832 — — — — — — — —

TABLE 3 Compounds of formula I, represented as compounds of formula A-Q wherein Q is Q₁, and Q₁ is the radical B39: B39 B39 B39 B39 B39 B39 B39 B39 B39 B39 B39 B39 A1 A2 A3 A4 A5 A6 A7 A18 A19 A20 A21 A22 A23 A24 A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36 A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48 A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60 A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A71 A72 A73 A74 A75 A76 A77 A78 A79 A80 A81 A82 A83 A84 A85 A86 A87 A88 A89 A90 A91 A92 A93 A94 A95 A96 A97 A98 A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120 A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132 A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144 A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156 A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168 A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180 A181 A182 A183 A184 A185 A186 A187 A188 A189 A200 A201 A202 A203 A204 A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216 A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228 A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240 A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252 A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264 A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276 A277 A278 A279 A280 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300 A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312 A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324 A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336 A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348 A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360 A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A382 A383 A384 A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396 A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408 A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420 A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432 A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444 A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456 A457 A458 A459 A460 A461 A462 A473 A474 A475 A476 A477 A478 A479 A480 A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492 A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504 A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516 A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528 A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540 A541 A542 A543 A544 A545 A546 A547 A548 A549 A550 A551 A552 A553 A564 A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576 A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588 A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600 A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612 A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624 A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636 A637 A638 A639 A640 A641 A642 A643 A654 A655 A656 A657 A658 A659 A660 A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672 A673 A674 A675 A676 A677 A678 A679 A680 A681 A682 A683 A684 A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696 A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708 A709 A710 A711 A712 A713 A714 A715 A716 A717 A718 A719 A720 A721 A722 A723 A724 A725 A726 A727 A728 A729 A730 A731 A732 A733 A744 A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756 A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768 A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780 A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792 A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804 A805 A806 A807 A808 A809 A810 A811 A812 A813 A814 A815 A816 A817 A828 A829 A830 A831 A832 — — — — — — — —

TABLE 4 Compounds of formula I, represented as compounds of formula A-Q wherein Q is Q₁, and Q₁ is the radical B3: B3 B3 B3 B3 B3 B3 B3 B3 B3 B3 B3 B3 — — — — — — — A18 A19 A20 A21 A22 A23 A24 A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36 A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48 A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60 A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A71 A72 A73 A74 A75 A76 A77 A78 A79 A80 A81 A82 A83 A84 A85 A86 A87 A88 A89 A90 — — — — — — — — A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120 A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132 A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144 A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156 A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168 A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180 A181 A182 A183 A184 A185 A186 A187 A188 A189 A200 A201 A202 A203 A204 A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216 A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228 A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240 A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252 A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264 A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276 A277 A278 A279 A280 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300 A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312 A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324 A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336 A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348 A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360 A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A382 A383 A384 A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396 A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408 A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420 A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432 A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444 A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456 A457 A458 A459 A460 A461 A462 A473 A474 A475 A476 A477 A478 A479 A480 A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492 A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504 A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516 A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528 A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540 A541 A542 A543 A544 A545 — — — — — — — — A564 A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576 A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588 A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600 A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612 A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624 A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636 — — — — — — — A654 A655 A656 A657 A658 A659 A660 A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672 A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696 A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708 A709 A710 A711 A712 A713 A714 A715 A716 A717 A718 A719 A720 A721 A722 A723 A724 A725 A726 — — — — — — A733 A744 A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756 A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768 A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780 A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792 A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804 A805 A806 A807 A808 A809 A810 A811 A812 A813 A814 A815 A816 A817 A828 A829 A830 A831 A832 — — — — — — — —

TABLE 5 Compounds of formula I, represented as compounds of formula A-Q wherein Q is Q₂, and Q₂ is the radical C5: C5 C5 C5 C5 C5 C5 C5 C5 C5 C5 C5 C5 A1 A2 A3 A4 A5 A6 A7 A8 A9 A10 A11 A12 A13 A14 A15 A16 A17 A18 A19 A20 A21 A22 A23 A24 A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36 A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48 A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60 A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A71 A72 A73 A74 A75 A76 A77 A78 A79 A80 A81 A82 A83 A84 A85 A86 A87 A88 A89 A90 A91 A92 A93 A94 A95 A96 A97 A98 A99 A100 A101 A102 A103 A104 A105 A106 A107 A108 A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120 A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132 A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144 A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156 A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168 A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180 A181 A182 A183 A184 A185 A186 A187 A188 A189 A190 A191 A192 A193 A194 A195 A196 A197 A198 A199 A200 A201 A202 A203 A204 A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216 A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228 A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240 A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252 A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264 A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276 A277 A278 A279 A280 A281 A282 A283 A284 A285 A286 A287 A288 A289 A290 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300 A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312 A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324 A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336 A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348 A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360 A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A372 A373 A374 A375 A376 A377 A378 A379 A380 A381 A382 A383 A384 A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396 A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408 A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420 A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432 A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444 A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456 A457 A458 A459 A460 A461 A462 A463 A464 A465 A466 A467 A468 A469 A470 A471 A472 A473 A474 A475 A476 A477 A478 A479 A480 A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492 A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504 A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516 A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528 A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540 A541 A542 A543 A544 A545 A546 A547 A548 A549 A550 A551 A552 A553 A554 A555 A556 A557 A558 A559 A560 A561 A562 A563 A564 A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576 A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588 A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600 A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612 A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624 A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636 A637 A638 A639 A640 A641 A642 A643 A644 A645 A646 A647 A648 A649 A650 A651 A652 A653 A654 A655 A656 A657 A658 A659 A660 A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672 A673 A674 A675 A676 A677 A678 A679 A680 A681 A682 A683 A684 A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696 A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708 A709 A710 A711 A712 A713 A714 A715 A716 A717 A718 A719 A720 A721 A722 A723 A724 A725 A726 A727 A728 A729 A730 A731 A732 A733 A734 A735 A736 A737 A738 A739 A740 A741 A742 A743 A744 A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756 A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768 A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780 A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792 A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804 A805 A806 A807 A808 A809 A810 A811 A812 A813 A814 A815 A816 A817 A818 A819 A820 A821 A822 A823 A824 A825 A826 A827 A828 A829 A830 A831 A832 — — — — — — — —

TABLE 6 Compounds of formula I, represented as compounds of formula A-Q wherein Q is Q₂, and Q₂ is the radical C2: C2 C2 C2 C2 C2 C2 C2 C2 C2 C2 C2 C2 A1 A2 A3 A4 A5 A6 A7 A8 A9 A10 A11 A12 A13 A14 A15 A16 A17 A18 A19 A20 A21 A22 A23 A24 A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36 A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48 A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60 A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A71 A72 A73 A74 A75 A76 A77 A78 A79 A80 A81 A82 A83 A84 A85 A86 A87 A88 A89 A90 A91 A92 A93 A94 A95 A96 A97 A98 A99 A100 A101 A102 A103 A104 A105 A106 A107 A108 A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120 A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132 A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144 A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156 A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168 A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180 A181 A182 A183 A184 A185 A186 A187 A188 A189 A190 A191 A192 A193 A194 A195 A196 A197 A198 A199 A200 A201 A202 A203 A204 A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216 A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228 A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240 A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252 A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264 A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276 A277 A278 A279 A280 A281 A282 A283 A284 A285 A286 A287 A288 A289 A290 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300 A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312 A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324 A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336 A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348 A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360 A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A372 A373 A374 A375 A376 A377 A378 A379 A380 A381 A382 A383 A384 A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396 A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408 A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420 A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432 A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444 A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456 A457 A458 A459 A460 A461 A462 A463 A464 A465 A466 A467 A468 A469 A470 A471 A472 A473 A474 A475 A476 A477 A478 A479 A480 A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492 A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504 A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516 A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528 A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540 A541 A542 A543 A544 A545 A546 A547 A548 A549 A550 A551 A552 A553 A554 A555 A556 A557 A558 A559 A560 A561 A562 A563 A564 A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576 A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588 A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600 A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612 A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624 A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636 A637 A638 A639 A640 A641 A642 A643 A644 A645 A646 A647 A648 A649 A650 A651 A652 A653 A654 A655 A656 A657 A658 A659 A660 A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672 A673 A674 A675 A676 A677 A678 A679 A680 A681 A682 A683 A684 A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696 A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708 A709 A710 A711 A712 A713 A714 A715 A716 A717 A718 A719 A720 A721 A722 A723 A724 A725 A726 A727 A728 A729 A730 A731 A732 A733 A734 A735 A736 A737 A738 A739 A740 A741 A742 A743 A744 A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756 A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768 A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780 A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792 A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804 A805 A806 A807 A808 A809 A810 A811 A812 A813 A814 A815 A816 A817 A818 A819 A820 A821 A822 A823 A824 A825 A826 A827 A828 A829 A830 A831 A832 — — — — — — — —

TABLE 7 Compounds of formula I, represented as compounds of formula A-Q wherein A is A10: A10 A10 A10 A10 A10 A10 A10 A10 A10 A10 A10 A10 C1 — C3 C4 — C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 — — — — — — — — —

TABLE 8 Compounds of formula I, represented as compounds of formula A-Q wherein A is A556: A556 A556 A556 A556 A556 A556 A556 A556 A556 A556 A556 A556 C1 — C3 C4 — C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 — — — — — — — — —

TABLE 8 Compounds of formula I, represented as compounds of formula A-Q wherein A is A646: A646 A646 A646 A646 A646 A646 A646 A646 A646 A646 A646 A646 C1 — C3 C4 — C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 — — — — — — — — —

Compounds of formulae 2.1 and 2.3 to 2.13.c are known by the names imazamox, imazethapyr, imazaquin, imazapyr, dimethenamid, atrazine, terbuthylazine, simazine, terbutryn, cyanazine, ametryn, terbumeton, prohexadione calcium, sethoxydim, clethodim, tepraloxydim, flumetsulam, metosulam, pyridate, bromoxynil, ioxynil, sulcotrione, carfentrazone, sulfentrazone, isoxaflutole, glufosinate, primisulfuron, prosulfuron, rimsulfuron, halosulfuron, nicosulfuron, ethoxysulfuron, flazasulfuron, triasulfuron, tralkoxydim, chlorsulfuron and thifensulfuron-methyl and are described in the Pesticide Manual, eleventh ed., British Crop Protection Council, 1997 under the entry numbers 412, 415, 414, 413, 240, 34, 692, 651, 693, 168, 20, 691, 595, 648, 146, 49, 339, 495, 626, 88, 425, 664, 112, 665, 436, 382, 589, 613, 644, 389, 519, 287, 325, 723, 717, 139 and 704. The compound of formula 2.13 wherein Y₂, Y₃ and Y₄ are methine, Y, is C—I, R₇₄ is COOMe, Y₅ is nitrogen, Y₆ is methyl and Y₇ is methoxy is known by the name iodosulfuron (especially the sodium salt) from AGROW No. 296, 16th January 1998, page 22. The compound of formula 2.13 wherein Y₁, Y₂, Y₃ and Y₄ are methine, R₇₄ is trifluoromethyl, Y₅ is nitrogen, Y₆ is trifluoromethyl and Y₇ is methoxy is known by the name tritosulfuron and is described in DE-A-40 38 430. The compound of formula 2.13 wherein Y₂ is NH—CHO, Y₁, Y₃ and Y₄ are methine, R₇₄ is CONMe₂, Y₅ is methine and Y₆ and Y₇ are methoxy is known by the name foramsulfuron and is described, for example, in WO 95/29899.

The compound of formula 2.13 wherein Y₂ is C—CH₂—NH—SO₂CH₃, Y₁, Y₃ and Y₄ are methine, R₇₄ is COOMe, Y₅ is methine, and Y₆ and Y₇ are methoxy, is known by the name mesosulfuron and is described, for example, under Chemical Abstracts Registry Number 208465-21-8.

Dichlorprop is described under Chemical Abstracts Registry Number 15165-67-0.

The S enantiomer of the compound of formula 2.12 is registered under the CAS-Reg. No. [35597-44-5]. The compound of the general formula 2.2, aRS,1′S(-)N-(1′-methyl-2′-methoxy-ethyl)-N-chloroacetyl-2-ethyl-6-methylaniline, and a compound of the general formula 2.3, (1S,aRS)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)-acetamide, are described, for example, in WO 97/34485. The compound of formula 2.9 wherein R₆₉ is NO₂ is known by the name mesotrione and is described, for example, in U.S. Pat. No. 5,006,158. The compound of formula 2.6 wherein R₆₂ is ethoxy, R₆₃ is fluorine, Y is methine, R₆₄ is methoxycarbonyl, R₆₅ is hydrogen and R₆₆ is chlorine is known by the name cloransulam, for example from AGROW No. 261, 2nd August 1996, page 21. The compound of formula 2.6 wherein R₆₂ is methoxy, R₆₃ is hydrogen, Y is C—F, R₆₄ is fluorine, R₆₅ is hydrogen and R₆₆ is fluorine is known by the name florasulam and is described in U.S. Pat. No. 5,163,995.

The following compounds of the composition according to the invention are described in the Pesticide Manual, eleventh ed., British Crop Protection Council, 1997: Compound of Pesticide Manual formula and/or name eleventh ed., Entry No.: 2.14 (metribuzin) 497 2.15 (aclonifen) 8 2.16 (glyphosate) 383 2.17 (bentazone) 65 2.18 (pendimethalin) 557 2.19 (dicamba) 210 2.20 (butylate) 100 2.22 (clomazone) 150 2.23 (2,4-D) 192 2.24 (flumiclorac) 340 2.25 (fluthiacet-methyl) 359 2.26 (flurtamone) 356 2.27 (flumioxazin) 341 2.28 (paraquat) 550 2.29 (azafenidin) 37 2.30 (fluthiamide) 51 2.33 (sulfosate) 383 2.34 (asulam) 33 2.35 (norflurazon) 526 2.36 (terbacil) 689 2.37 (thiazopyr) 702 2.38 (dithiopyr) 259 2.39 (hexazinone) 400 2.40 (diuron) 260 2.41 (MCPA) 455 2.42 (mecoprop) 459 2.43 (tebuthiuron) 683 prosulfocarb 612 pyraflufen-ethyl 617 fenoxaprop-P-ethyl 309 diclofop-methyl 219 amidosulfuron 21 flupyrsulfuron 348 flupyrsulfuron-methyl-sodium 348 metsulfuron-methyl 498 sulfosulfuron 668 tribenuron-methyl 728 imazamethabenz-methyl 411 chlorotoluron 134 isoproturon 433 methabenzthiazuron 477 bifenox 69 fluoroglycofen-ethyl 344 imazosulfuron 416 diflufenican 232 bilanafos 71 ethalfluralin 279 trifluralin 740 fluthiamid 51 isoxaben 435 triallate 722 2,4-DB 199 MCPB 457 clopyralid 153 fluroxypyr 354 quinmerac 636 benazolin-ethyl 55 difenzoquat 229 dithiopyr 259 quinclorac 635 prodiamine 593 benefin 57

The following compounds of the composition according to the invention are described in the Pesticide Manual, 12th ed., British Crop Protection Council, 2000: Pesticide Manual Compound 12th ed., Entry No.: picolinafen 621 beflubutamid 57 flucarbazone 357 cyhalofop-butyl 191

The compound of formula 2.7 wherein R₆₇ is hydrogen and its preparation are described in U.S. Pat. No. 3,790,571; the compound of formula 2.6 wherein R₆₂ is ethoxy, Z is nitrogen, R₆₃ is fluorine, R₆₄ is chlorine and R₆₅ is hydrogen and R₆₆ is chlorine is described in U.S. Pat. No. 5,498,773.

The compound of formula 2.21 and its preparation are described in U.S. Pat. No. 5,183,492; the compound of formula 2.22 is described, under the name isoxachlortole, in AGROW No. 296, 16th January 1998, page 22. The compound of formula 2.31 is described, under the name fentrazamide, in The 1997 British Crop Protection Conference—Weeds, Conference Proceedings Vol. 1, 2-8, pages 67 to 72; the compound of formula 2.32 is described, under the name JV 485 (isoxapropazol), in The 1997 British Crop Protection Conference—Weeds, Conference Proceedings Vol. 1, 3A-2, pages 93 to 98. The compound of formula 2.44 is known by the name pethoxamid and is described, for example, in EP-A-0 206 251. The compound of formula 2.45 is known by the name procarbazone and is described, for example, in EP-A-0 507 171; the compound of formula 2.46 is known by the name fluazolate and is described, for example, in U.S. Pat. No. 5,530,126. The compound of formula 2.47 is known by the name cinidon-ethyl and is described, for example, in DE-A-40 37 840. The compound of formula 2.48 is known by the name benzfendizone and is described, for example, in WO 97/08953. The compound of formula 2.49 is known as diflufenzopyr and is described, for example, in EP-A-0 646 315. The compound of formula 2.50 (amicarbazone) and its preparation are disclosed in DD 298 393 and in U.S. Pat. No. 5,194,085. The compound of formula 2.51 (flufenpyr-ethyl) is described in Abstracts of Papers American Chemical Society, (2000) Vol. 220, No. Part 1, pp. AGRO 174. The compounds of formula 2.52 are described in WO 01/17352; the compound of formula 2.53 is described in U.S. Pat. No. 4,881,966.

It is extremely surprising that the combination of the compound of formula I with one or more active ingredients selected from formulae 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amido-sulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin exceeds the additive effect on the weeds to be controlled that is to be expected in principle and thus broadens the range of action of the individual active ingredients especially in two respects: firstly, the rates of application of the individual compounds of formulae I and 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin are reduced while a good level of action is maintained and, secondly, the composition according to the invention achieves a high level of weed control also in those cases where the individual substances, in the low rates of application range, have become useless from the agronomic standpoint. The result is a considerable broadening of the spectrum of weeds and an additional increase in selectivity in respect of the crops of useful plants, as is necessary and desirable in the event of an unintentional overdose of active ingredient. The composition according to the invention, while retaining excellent control of weeds in crops of useful plants, also allows greater flexibility in succeeding crops.

The composition according to the invention can be used against a large number of agronomically important weeds, such as Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica. The composition according to the invention is suitable for all methods of application convention-ally used in agriculture, e.g. pre-emergence application, post-emergence application and seed dressing. The composition according to the invention is suitable especially for controlling weeds in crops of useful plants, such as cereals, rape, sugar beet, sugar cane, plantation crops, rice, maize and soybeans, and also for non-selective weed control.

“Crops” are to be understood to mean also those crops which have been made tolerant to herbicides or classes of herbicides (Ie.g. HPPD-inhibitors, ALS-inhibitors, EPSPS-(5-enol-pyruvyl-shikimate-3-phosphate-synthease)inhibitors or GS—(glutamine-synthease)inhibitors) as a result of conventional methods of breeding or genetic engineering. Examples for crops which have been made tolerant to imidazolinone as a result of conventional methods of breeding (mutagenese) is Clearfiled® canola. An example for crops which have been made tolerant to herbicides or classes of herbicides as a result of genetic engineering are maize seeds which are resistant to glyphosate and glufosinate respectively, commercially available under the brand Roundup Ready® and Liberty Link®.

The composition according to the invention comprises the compound of formula I and the compounds of formulae 2.1 to 2.53 and prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin in any mixing ratio, but usually has an excess of one component over the others. Generally, the mixing ratios (ratios by weight) of the compound of formula I and the mixing partners of formulae 2.1 to 2.53 and prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin are from 1:2000 to 2000:1, especially from 200:1 to 1:200.

The rate of application may vary within wide limits and depends on the nature of the soil, the method of application (pre- or post-emergence; seed dressing; application to the seed furrow; no tillage application etc.), the crop plant, the weed to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. The active ingredient mixture according to the invention can generally be applied at a rate of from 1 to 5000 g of active ingredient mixture/ha.

The mixtures of the compound of formula I with the compounds of formulae 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin may be used in unmodified form, that is to say as obtained in the synthesis. Preferably, however, they are formulated in customary manner, together with the adjuvants conventionally used in formulation technology, such as solvents, solid carriers or surfactants, for example into emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

The formulations, i.e. the compositions, preparations or mixtures comprising the compounds of formulae I and 2.1 to 2.53 and prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin and also, where appropriate, one or more solid or liquid formulation adjuvants, are prepared in a manner known per se, e.g. by intimately mixing and/or grinding the active ingredients with the formulation adjuvants, e.g. solvents or solid carriers. In addition, surface-active compounds (surfactants) may also be used in the preparation of the formulations.

Examples of solvents and solid carriers are given, for example, in WO 97/34485, page 6.

Depending on the nature of the compound of formula I to be formulated, suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties.

Examples of suitable anionic, non-ionic and cationic surfactants are listed, for example, in WO 97/34485, pages 7 and 8.

Also suitable in the preparation of the herbicidal compositions according to the invention are the surfactants conventionally used in formulation technology, which are described, inter alia, in “McCutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch”, Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-III, Chemical Publishing Co., New York, 1980-81.

The compositions according to the invention may additionally comprise an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives.

In the composition according to the invention, the amounts of oil additive employed are generally from 0.01 to 2%, based on the spray mixture. The oil additive can, for example, be added to the spray tank in the desired concentration after the spray mixture has been prepared.

Preferred oil additives comprise mineral oils or an oil of vegetable origin such as, for example, rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, such as AMIGO® obtainable from Rhône-Poulenc Canada Inc., alkyl esters of oils of vegetable origin such as, for example, the methyl derivatives, or an oil of animal origin such as fish oil or beef tallow. Especially preferred is the “additive type A”, which contains as active components essentially 80% by weight of alkyl esters of fish oils and 15% by weight of methylated rapeseed oil, and also 5% by weight of customary emulsifiers and pH modifiers.

Especially preferred oil additives comprise alkyl esters of higher fatty acids (C₈-C₂₂), especially the methyl derivatives of C₁₂-C₁₈ fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid. Those esters are known as methyl laurate (CAS-111-82-0), methyl palmitate (CAS-112-39-0) and methyl oleate (CAS-112-62-9). A preferred fatty acid methyl ester derivative is Emery® 2230 and 2231 (Henkel subsidiary company Cognis GmbH, DE).

The application and action of the oil additives can be improved by combining them with surface-active substances such as non-ionic, anionic or cationic surfactants. Examples of suitable anionic, non-ionic and cationic surfactants are listed in WO 97/34485 on pages 7 and 8.

Preferred surface-active substances are anionic surfactants of the dodecylbenzylsulfonate type, especially the calcium salts thereof, and also non-ionic surfactants of the fatty alcohol ethoxylate type. Special preference is given to ethoxylated C₁₂-C₂₂ fatty alcohols having a degree of ethoxylation of from 5 to 40. Examples of commercially available preferred surfactants are the Genapol types (Clariant AG, Muttenz, Switzerland). The concentration of the surface-active substances based on the total additive is generally from 1 to 30% by weight.

Surface-active substances the use of which is likewise preferred are silicone surfactants, especially polyalkyl-oxide-modified heptamethyltrisiloxanes, such as are obtainable commercially as, for example, Silwet L-77®, and also perfluorinated surfactants.

Examples of oil additives consisting of mixtures of oils or mineral oils or derivatives thereof with surfactants are Edenor ME SU®, Turbocharge® (Zeneca Agro, Stoney Creek, Ontario, CA) or, more especially, Actipron® (BP Oil UK Limited, GB).

The addition of an organic solvent to the oil additive/surfactant mixture can, furthermore, bring about a further increase in action. Suitable solvents are, for example, Solvesso®(ESSO) or Aromatic Solvent®) (Exxon Corporation) types. The concentration of those solvents can be from 10 to 80% of the total weight.

Such oil additives, which are also described, for example, in U.S. Pat. No. 4,834,908, are especially preferred for the composition according to the invention. An especially preferred oil additive is known under the name MERGE®, it can be obtained from the BASF Corporation and a basic description thereof is given, for example, in U.S. Pat. No. 4,834,908 in col. 5, as Example COC-1. A further oil additive that is preferred according to the invention is SCORE® (Novartis Crop Protection Canada).

In addition to the above-listed oil additives, formulations of alkylpyrrolidones such as are marketed commercially, for example as Agrimax®, may additionally be added to the spray mixture in order to enhance the action of the compositions according to the invention. There may likewise be used, for the purpose of enhancing action, formulations of synthetic latices, for example polyacrylamide, polyvinyl compounds or poly-1-p-menthene, such as are available on the market as, for example, Bond®, Courier® or Emerald®. In addition, propionic acid-containing solutions, such as Eurogkem Pen-e-trate®, may be added to the spray mixture as action-enhancing agents.

To the compositions according to the invention comprising the compounds of formulae 2.52 there are preferably added one or more of the above-listed oil additives or of the above-listed alkylpyrrolidone formulations, synthetic latices or propionic acid-containing solutions.

The herbicidal formulations usually contain from 0.1 to 99% by weight, especially from 0.1 to 95% by weight, of active ingredient mixture comprising a compound of formula I together with the compounds of formulae 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenz-thiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin, from 1 to 99.9% by weight of a solid or liquid formulation adjuvant, and from 0 to 25% by weight, especially from 0.1 to 25% by weight, of a surfactant.

Whereas commercial products are usually formulated as concentrates, the end user will normally employ dilute formulations. The compositions may also comprise further ingredients, such as stabilisers, e.g. vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders, tackifiers, and also fertilisers or other active ingredients. Preferred formulations have especially the following compositions:

(%=percent by weight)

Emulsifiable Concentrates:

-   active ingredient mixture: 1 to 90%, preferably 5 to 20% -   surfactant: 1 to 30%, preferably 10 to 20% -   liquid carrier: 5 to 94%, preferably 70 to 85%     Dusts: -   active ingredient mixture: 0.1 to 10%, preferably 0.1 to 5% -   solid carrier: 99.9 to 90%, preferably 99.9 to 99%     Suspension Concentrates: -   active ingredient mixture: 5 to 75%, preferably 10 to 50% -   water: 94 to 24%, preferably 88 to 30% -   surfactant: 1 to 40%, preferably 2 to 30%     Wettable Powders: -   active ingredient mixture: 0.5 to 90%, preferably 1 to 80% -   surfactant: 0.5 to 20%, preferably 1 to 15% -   solid carrier: 5 to 95%, preferably 15 to 90%     Granules: -   active ingredient mixture: 0.1 to 30%, preferably 0.1 to 15% -   solid carrier: 99.5 to 70%, preferably 97 to 85%

The following Examples illustrate the invention further, but do not limit the invention. F1. Emulsifiable concentrates a) b) c) d) active ingredient mixture  5% 10% 25% 50% calcium dodecylbenzenesulfonate  6%  8%  6% 8% castor oil polyglycol ether  4% —  4% 4% (36 mol of ethylene oxide) octylphenol polyglycol ether —  4% — 2% (7-8 mol of ethylene oxide) cyclohexanone — — 10% 20% arom. hydrocarbon mixture 85% 78% 55% 16% C₉-C₁₂

Emulsions of any desired concentration can be obtained from such concentrates by dilution with water. F2. Solutions a) b) c) d) active ingredient mixture  5% 10% 50% 90% 1-methoxy-3-(3-methoxy- — 20% 20% — propoxy)-propane polyethylene glycol MW 400 20% 10% — — N-methyl-2-pyrrolidone — — 30% 10% arom. hydrocarbon mixture 75% 60% — — C₉-C₁₂

The solutions are suitable for use in the form of microdrops. F3. Wettable powders a) b) c) d) active ingredient mixture  5% 25% 50% 80% sodium lignosulfonate  4% —  3% — sodium lauryl sulfate  2%  3% —  4% sodium diisobutylnaphthalene- —  6%  5%  6% sulfonate octylphenol polyglycol ether —  1%  2% — (7-8 mol of ethylene oxide) highly dispersed silicic acid  1%  3%  5% 10% kaolin 88% 62% 35% —

The active ingredient is mixed thoroughly with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of any desired concentration. F4. Coated granules a) b) c) active ingredient mixture 0.1% 5% 15% highly dispersed silicic acid 0.9% 2% 2% inorganic carrier 99.0% 93% 83% (diameter 0.1-1 mm) e.g. CaCO₃ or SiO₂

The active ingredient is dissolved in methylene chloride and applied to the carrier by spraying, and the solvent is then evaporated off in vacuo. F5. Coated granules a) b) c) active ingredient mixture 0.1% 5% 15% polyethylene glycol MW 200 1.0% 2% 3% highly dispersed silicic acid 0.9% 1% 2% inorganic carrier 98.0% 92% 80% (diameter 0.1-1 mm) e.g. CaCO₃ or SiO₂

The finely ground active ingredient is uniformly applied, in a mixer, to the carrier moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner. F6. Extruder granules a) b) c) d) active ingredient mixture 0.1% 3% 5% 15% sodium lignosulfonate 1.5% 2% 3% 4% carboxymethylcellulose 1.4% 2% 2% 2% kaolin 97.0% 93% 90% 79%

The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air. F7. Dusts a) b) c) active ingredient mixture 0.1% 1% 5% talcum 39.9% 49% 35% kaolin 60.0% 50% 60%

Ready-to-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture in a suitable mill. F8. Suspension concentrates a) b) c) d) active ingredient mixture   3%  10%  25%  50% ethylene glycol   5%   5%   5%   5% nonylphenol polyglycol ether —   1%   2% — (15 mol of ethylene oxide) sodium lignosulfonate   3%   3%   4%   5% carboxymethylcellulose   1%   1%   1%   1% 37% aqueous formaldehyde 0.2% 0.2% 0.2% 0.2% solution silicone oil emulsion 0.8% 0.8% 0.8% 0.8% water  87%  79%  62%  38%

The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.

It is often more practical for the compound of formula I and the mixing partner or partners of formulae 2.1 to 2.53 and prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin to be formulated separately and to be brought together in the desired mixing ratio in the applicator in the form of a “tank mixture” in water shortly before application.

The compositions according to the invention may additionally comprise growth regulators, such as, for example, trinexapac (744), chlormequat chloride (129), clofencet (148), cyclanilide (170), ethephon (281), flurprimidol (355), gibberellic acid (379), inabenfide (421), maleic hydrazide (449), mefluidide (463), mepiquat chloride (465), paclobutrazol (548), prohexadione-calcium (595), uniconazole (746) or thidiazuron (703). Fungicides, such as, for example, azoxystrobin (43), epoxiconazole (48), benomyl (60), bromuconazole (89), bitertanol (77), carbendazim (107), cyproconazole (189), cyprodinil (190), diclomezine (220), difenoconazole (228), diniconazole (247), epoxiconazole (48), ethirimol (284), etridiazole (294), fenarimol (300), fenbuconazole (302), fenpiclonil (311), fenpropidin (313), fenpropimorph (314), ferimzone (321), fludioxonil (334), fluquinconazole (349), flutolanil (360), flutriafol (361), imazalil (410), ipconazole (426), iprodione (428), isoprothiolane (432), kasugamycin (438), kresoxim-methyl (439), spiroxamine (441), mepronil (466), myclobutanil (505), nuarimol (528), pefurazoate (554), pencycuron (556), phthalide (576), probenazole (590), prochloraz (591), propiconazole (607), pyrazophos (619), pyroquilon (633), quinoxyfen (638), quintozene (639), tebuconazole (678), tetraconazole (695), thiabendazole (701), thifluzamide (705), triadimefon (720), triadimenol (721), tricyclazole (734), tridemorph (736), triflumizole (738), triforine (742), triticonazole (745) or vinclozolin (751), may also be present in the compositions according to the invention. The number in parentheses after each active ingredient indicates the entry number of the active ingredient in the Pesticide Manual, eleventh ed., British Crop Protection Council, 1997.

Biological Examples:

A synergistic effect exists whenever the action of the active ingredient combination of the compound of formula I with compounds of formulae 2.1 to 2.53 and prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin is greater than the sum of the actions of the active ingredients applied separately.

The herbicidal action to be expected We for a given combination of two herbicides can be calculated as follows (see COLBY, S. R., “Calculating synergistic and antagonistic response of herbicide combinations”, Weeds 15, pages 20-22, 1967: We=X+[Y•(100−X)/100] wherein:

X=percentage herbicidal action on treatment with the compound of formula I at a rate of application of p kg per hectare, compared with the untreated control (=0%).

Y=percentage herbicidal action on treatment with a compound of formula 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chloro-toluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin at a rate of application of q kg per hectare, compared with the untreated control.

We=expected herbicidal action (percentage herbicidal action compared with the untreated control) following treatment with the compounds of formulae I and 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin at a rate of application of p+q kg of active ingredient per hectare.

When the action actually observed is greater than the value to be expected We, there is a synergistic effect.

The synergistic effect of the combinations of a compound of formula I with the compounds of formulae 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin is demonstrated in the following Examples.

Experiment Description—Pre-Emergence Test:

Monocotyledonous and dicotyledonous test plants are sown in standard soil in plastics pots. Directly after sowing, the test compounds are applied in aqueous suspension by spraying (500 litres of water/ha). The rates of application depend on the optimum concentrations determined under field conditions and greenhouse conditions. The test plants are then grown in the greenhouse under optimum conditions. The tests are evaluated after 36 days (% action, 100%=plant has died, 0%=no phytotoxic action). The mixtures used in this test exhibit good results.

Experiment Description—Post-Emergence Test:

The test plants are grown to the 2- to 3-leaf stage in plastics pots under greenhouse conditions. A standard soil is used as cultivation substrate. At the 2- to 3-leaf stage, the herbicide is applied to the test plants both alone and in admixture. Application is carried out using an aqueous suspension of the test compounds in 500 litres of water/ha. The rates of application depend on the optimum concentrations determined under field conditions and greenhouse conditions. The tests are evaluated after 33 days (% action, 100%=plant has died, 0%=no phytotoxic action). In this test, too, the mixtures used exhibit good results.

It has been shown, surprisingly, that specific safeners are suitable for mixing with the synergistic composition according to the invention. The present invention accordingly relates also to a selectively herbicidal composition for controlling grasses and weeds in crops of useful plants, especially in maize crops, that comprises a compound of formula I, one or more compounds selected from the compounds of formulae 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin, and a safener (counter agent, antidote) that protects the useful plants, but not the weeds, against the phytotoxic action of the herbicide, as well as to the use of such a composition in the control of weeds in crops of useful plants.

There is accordingly also proposed in accordance with the invention a selectively herbicidal composition that, in addition to comprising customary inert formulation adjuvants, such as carriers, solvents and wetting agents, comprises as active ingredient a mixture of a) an amount, effective for herbicide synergism, of the compound of formula I and one or more compounds selected from the compounds of formulae 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin, and b) an amount, effective for herbicide antagonism, of a compound selected from the compound of formula 3.1

and the compound of formula 3.2

and the compound of formula 3.3

the free acid thereof and salts and hydrates thereof,

-   and the compound of formula 3.4     and the compound of formula 3.5     and the compound of formula 3.6     and the compound of formula 3.7     and the compound of formula 3.8     and of formula 3.9     Cl₂CHCON(CH₂CH═CH₂)₂  (3.9),     and of formula 3.10     and of formula 3.11     and of formula 3.12     and methyl and ethyl esters thereof and salts thereof, especially     the sodium salt, -   and of formula 3.13     and of formula 3.14     and of formula 3.15     and of formula 3.16     and of formula 3.17

The invention relates also to a selectively herbicidal composition that, in addition to comprising customary inert formulation adjuvants, such as carriers, solvents and wetting agents, comprises as active ingredient a mixture of

-   a) a herbicidally effective amount of the compound of formula I and -   b) an amount, effective for herbicide antagonism, of a compound     selected from the compounds of formulae 3.1, 3.2, 3.3, 3.4, 3.5,     3.6, 3.7, 3.8, 3.9, 3.10, 3.11, 3.12, 3.13, 3.14, 3.15, 3.16 and     3.17.

Preferred compositions according to the invention comprise as safener a compound selected from the compounds of formulae 3.1, 3.3 and 3.8. Such safeners are suitable especially for the compositions according to the invention that comprise the above-mentioned preferred compounds of formulae 2.1 to 2.53 or prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin.

Preferred compositions according to the invention also comprise an amount, effective for herbicide antagonism, of 2-(5-chloroquinolin-8-yloxy)acetic acid-1-methyl hexyl ester of formula 3.3, or a hydrate thereof, especially 1-methylhexyl-(5-chloroquinolin-8-yloxy)acetate tetrahydrate, the free acid thereof or a salt thereof of formula

wherein M is a mono-, di- or tri-valent metal, ammonium, N(R)₄ or HN(R)₃, wherein the substituents R are identical to or different from one another and are C₁-C₁₆alkyl or C₁-C₁₆hydroxyalkyl, or M is S(R_(a))₃ or P(R_(a))₄, wherein the substituents R_(a) are identical to or different from one another and are C₁-C₂Oalkyl, C₂-C₂₀alkenyl, C₂-C₂₀alkynyl, aryl substituted by C₁-C₂₀alkyl, C₂-C₂₀alkenyl or by C₂-C₂₀alkynyl, or heteroaryl substituted by C₁-C₂₀alkyl, C₂-C₂₀alkenyl or by C₂-C₂₀alkynyl, or 2 substituents R_(a) together with the sulfur or phosphorus atom to which they are bonded form a 5- or 6-membered ring.

The metal atoms M that may be present in formula 3.3a are preferably those of alkali metals or alkaline earth metals, especially sodium, potassium, calcium, magnesium and also especially aluminium and iron as preferred examples of trivalent metals.

Of the alkyl and hydroxyalkyl substituents R, preference is given to those having from 12 to 16 carbon atoms and also to those having from 1 to 4 carbon atoms. The groups N(R)₄ and HN(R)₃ especially contain one long-chain and 2 or 3 short-chain alkyl groups, such as, for example, hexadecyl-triethylammonium, tetradecyl-triethylammonium, dodecyl-triethyl-ammonium, dodecyl-ethyl-dimethylammonium and also tetradodecylammonium. Preferred alkyl groups R_(a) contain from 1 to 12, especially from 1 to 6, carbon atoms. The alkyl groups R and R_(a) may themselves be substituted, for example by halogen, alkoxy or haloalkoxy, each of which preferably has from 1 to 4 carbon atoms. Preferred alkenyl and alkynyl groups R_(a) contain from 2 to 12 carbon atoms. They may contain more than one unsaturated bond and may be substituted by halogen, alkoxy or haloalkoxy, each of which preferably has from 1 to 4 carbon atoms. Suitable examples of aryl groups R_(a) are phenyl, naphthyl, tetrahydro-naphthyl, indanyl and indenyl, phenyl being preferred. Such groups may be substituted by the above-mentioned alkyl, alkenyl and alkynyl groups. There may be mentioned as heteroaryl groups R_(a) preferably 5- and 6-membered rings that contain especially nitrogen and/or oxygen atoms, such as, for example, pyridyl, pyrimidinyl, triazinyl, thienyl, thiazolyl, pyrazolyl, imidazolyl, piperidyl, dioxolanyl, morpholinyl and tetrahydrofuryl. Such heterocycles too may themselves be substituted by the above-mentioned alkyl, alkenyl and alkynyl groups. Groups of two R_(a) substituents may, together with the sulfur or phosphorus atom to which they are bonded, form a ring. Preferably, 5- or 6-membered, saturated rings are formed. The sulfonium and phosphonium cations that can be used according to the invention are described, for example, in WO 00/44227.

Preferred salts of 2-(5-chloroquinolin-8-yloxy)acetic acid-1-methyl hexyl ester comprise a compound of formula 3.3a wherein M is sodium, potassium or tri(hydroxyethylene)ammonium.

A further group of preferred salts of 2-(5-chloroquinolin-8-yloxy)acetic acid-1-methyl hexyl ester comprises those wherein, in formula 3.3a, M is calcium, magnesium, aluminium, iron, trimethylsulfonium, triphenylsulfonium, tetraphenylphosphonium, triphenyl-methyl-phosphonium, triphenyl-benzylphosphonium, C₁₂-C₁₆alkyl-trimethylammonium, C₁₂-C₁₆alkyl-triethylammonium, tetradodecylammonium or dodecyl-ethyl-dimethylammonium.

The salts of formula 3.3a can be prepared according to customary methods, for example by reaction of 2-(5-chloroquinolin-8-yloxy)acetic acid-1-methyl hexyl ester with an equimolar amount of a metal hydroxide in alcoholic solution at room temperature.

The salts listed in the following Table are obtainable in that manner: TABLE A Compounds of formula 3.3a: Compound No. M M.p. (° C.) 2.01 Na >250 2.02 K >265 2.03 Ca 2.04 Mg 2.05 NH₄ 227-228 2.06 NH(CH₂CH₂OH)₃ 132-152 2.07 N(C₁₂H₂₅)₄ 2.08 N(C₁₂H₂₅)(C₂H₅)(CH₃)₂ 2.09 N(C₁₂H₂₅)(CH₃)₃ 2.10 N(C₁₂H₂₅)(C₂H₅)₃ 2.11 Al 2.12 Fe 2.13 H 232-233 2.14 S(CH₃)₃ 2.15 S(C₆H₅)₃ 2.16 P(C₆H₅)₄ 2.17 P(C₆H₅)₃CH₃ 2.18 P(C₆H₅)₃CH₂C₆H₅

Further preferred compositions according to the invention comprise a compound of formula 2.53 and an amount, effective for herbicide antagonism, of 2-(5-chloroquinolin-8-yloxy)-1-methylhexyl ester of formula 3.3, or a hydrate thereof, especially 1-methylhexyl (5-chloroquinolin-8-yloxy)acetate tetrahydrate, the free acid thereof or a salt thereof of formula 3.3a.

Combinations of the compound of formula I with the compound of formula 3.1 have proved to be especially effective compositions. Such a composition is used preferably together with the compound of formula 2.2a

aRS,1′S(−)N-(1′-methyl-2′-methoxyethyl)-N-chloroacetyl-2-ethyl-6-methylaniline).

The invention relates also to a method for the selective control of weeds in crops of useful plants, which comprises treating the useful plants, seeds or cuttings thereof, or the area of cultivation thereof, with a herbicidally effective amount of the herbicide of formula I, optionally one or more herbicides selected from the compounds of formulae 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin, and an amount, effective for herbicide antagonism, of a safener from formulae 3.1 to 3.17.

The compounds of formulae 3.1 to 3.17 are known and are described, for example, in the Pesticide Manual, eleventh ed., British Crop Protection Council, 1997 under the entry numbers 61 (formula 3.1, benoxacor), 304 (formula 3.2, fenclorim), 154 (formula 3.3, cloquintocet), 462 (formula 3.4, mefenpyr-diethyl), 377 (formula 3.5, furilazole), 363 (formula 3.8, fluxofenim), 213 (formula 3.9, dichlormid) and 350 (formula 3.10, flurazole). The compound of formula 3.11 is known as MON 4660 (Monsanto) and is described, for example, in EP-A-0 436 483. The compound of formula 3.17 is described, for example, in U.S. Pat. No. 6,162,762.

The compound of formula 3.6 (AC 304415) is described, for example, in EP-A-0 613 618, and the compound of formula 3.7 in DE-A-29 48 535. The compounds of formula 3.12 are described in DE-A-43 31 448, and the compound of formula 3.13 in DE-A-35 25 205. The compound of formula 3.14 is known, for example, from U.S. Pat. No. 5,215,570, and the compound of formula 3.15 from EP-A-0 929 543. The compound of formula 3.17 is described in WO 99/00020. In addition to the compound of formula 3.17, the other 3-(5-tetrazolyl-carbonyl)-2-quinolones described in WO 99/00020, especially the compounds specifically disclosed in Tables 1 and 2 on pages 21 to 29, are also suitable for protecting crop plants against the phytotoxic action of the compounds of formula I.

As crop plants that can be protected by the safeners of formulae 3.1 to 3.17 against the damaging effect of the above-mentioned herbicides there come into consideration especially cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, more especially maize. “Crops” are to be understood to mean also those crops which have been made tolerant to herbicides or classes of herbicides as a result of conventional methods of breeding or genetic engineering.

The weeds to be controlled may be both monocotyledonous and dicotyledonous weeds, such as, for example Stellaria, Agrostis, Digitaria, Avena, Apera, Brachiaria, Phalaris, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Panicum, Bromus, Alopecurus, Sorghum halepense, Sorghum bicolor, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.

Areas of cultivation include the areas of ground on which the crop plants are already growing or which have been sown with the seeds of those crop plants, as well as ground intended for the cultivation of such crop plants.

Depending on the intended use, a safener of formula 3.1 to 3.17 can be used in the pretreatment of the seed of the crop plant (dressing of the seeds or cuttings) or can be introduced into the soil before or after sowing. It can, however, also be applied, either alone or together with the herbicide, after emergence of the plants. The treatment of the plants or seeds with the safener can therefore in principle be carried out independently of the time at which the herbicide is applied. The plants can, however, also be treated by simultaneous application of herbicide and safener (e.g. in the form of a tank mixture). The ratio of the rate of application of safener to the rate of application of herbicide depends largely on the method of application. In the case of field treatment, which is carried out either using a tank mixture comprising a combination of safener and herbicide or by separate application of safener and herbicide, the ratio of herbicides to safener is generally from 100:1 to 1:10, preferably from 20:1 to 1:1. In the case of field treatment it is usual to apply from 0.001 to 1.0 kg of safener/ha, preferably from 0.001 to 0.25 kg of safener/ha.

The rate of application of herbicides is generally from 0.001 to 5 kg/ha, but preferably from 0.005 to 0.5 kg/ha.

The compositions according to the invention are suitable for all methods of application conventionally used in agriculture, e.g. pre-emergence application, post-emergence application and seed dressing.

In the case of seed dressing, generally from 0.001 to 10 g of safener/kg of seed, preferably from 0.05 to 2 g of safener/kg of seed, are applied. When the safener is applied in liquid form shortly before sowing, with soaking of the seeds, then advantageously the safener solutions used contain the active ingredient in a concentration of from 1 to 10 000 ppm, preferably from 100 to 1000 ppm.

For the purpose of application, the safeners of formulae 3.1 to 3.17 or combinations of those safeners with a herbicide of formula I and optionally one or more herbicides selected from formulae 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin are advantageously formulated together with adjuvants customary in formulation technology, e.g. into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.

Such formulations are described, for example, in WO 97/34485, pages 9 to 13. The formulations are prepared in known manner, e.g. by intimately mixing and/or grinding the active ingredients with liquid or solid formulation adjuvants, e.g. solvents or solid carriers. In addition, surface-active compounds (surfactants) can also be used in the preparation of the formulations. Solvents and solid carriers suitable for that purpose are mentioned, for example, in WO 97/34485, page 6.

Depending on the nature of the compound of formulae I, 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin and 3.1 to 3.17 to be formulated, there come into consideration as surface-active compounds non-ionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties. Examples of suitable anionic, non-ionic and cationic surfactants are listed, for example, on pages 7 and 8 of WO 97/34485. Also suitable for the preparation of the herbicidal compositions according to the invention are the surfactants conventionally employed in formulation technology, which are described, inter alia, in “McCutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch”, Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash, “Encyclopedia of Surfactants”, Vol. I-III, Chemical Publishing Co., New York, 1980-81.

The herbicidal formulations usually contain from 0.1 to 99% by weight, especially from 0.1 to 95% by weight, of active ingredient mixture comprising the compound of formula I, a compound selected from the compounds of formulae 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin and the compounds of formulae 3.1 to 3.17, from 1 to 99.9% by weight of a solid or liquid formulation adjuvant and from 0 to 25% by weight, especially from 0.1 to 25% by weight, of a surfactant. Whereas commercial products are usually formulated as concentrates, the end user will normally employ dilute formulations.

The compositions may also comprise further ingredients, such as stabilisers, e.g. vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), anti-foams, e.g. silicone oil, preservatives, viscosity regulators, binders, tackifiers, and also fertilisers or other active ingredients. For the use of safeners of formulae 3.1 to 3.17, or of compositions comprising them, in the protection of crop plants against the damaging effects of herbicides of formulae I and 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenz-thiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin, various methods and techniques come into consideration, such as, for example, the following:

i) Seed Dressing

-   a) Dressing of the seeds with a wettable powder formulation of a     compound from formulae 3.1 to 3.17 by shaking in a vessel until     uniformly distributed over the seed surface (dry dressing). In that     procedure approximately from 1 to 500 g of compound from formulae     3.1 to 3.17 (4 g to 2 kg of wettable powder) are used per 100 kg of     seed. -   b) Dressing of the seeds with an emulsifiable concentrate of a     compound from formulae 3.1 to 3.17 according to method a) (wet     dressing). -   c) Dressing by immersing the seeds for from 1 to 72 hours in a     liquor comprising from 100 to 1000 ppm of a compound from formulae     3.1 to 3.17 and optionally subsequently drying the seeds (immersion     dressing).

Dressing the seed or treating the germinated seedling are naturally the preferred methods of application, because treatment with the active ingredients is directed entirely at the target crop. Generally from 1 to 1000 g of antidote, preferably from 5 to 250 g of antidote, are used per 100 kg of seed, but depending on the methodology, which also allows other active ingredients or micronutrients to be added, concentrations above or below the limits indicated may be employed (repeat dressing).

ii) Application as a Tank Mixture

A liquid formulation of a mixture of antidote and herbicide is used (ratio by weight of the one to the other from 10:1 to 1:100), the rate of application of herbicide being from 0.005 to 5.0 kg per hectare. Such tank mixtures are applied before or after sowing.

iii) Application to the Seed Furrow

The compound from formulae 3.1 to 3.17 is introduced into the open, sown seed furrow in the form of an emulsifiable concentrate, wettable powder or granules. Once the seed furrow has been covered over, the herbicide is applied in the usual manner pre-emergence.

iv) Controlled Release of Active Ingredient

The compound from formulae 3.1 to 3.17 is applied in solution to mineral carrier granules or polymerised granules (urea/formaldehyde) and dried. If desired, it is also possible to apply a coating that allows the active ingredient to be released in metered amounts over a specific period of time (coated granules).

Preferred formulations have especially the following compositions:

(%=percent by weight)

Emulsifiable Concentrates:

-   active ingredient mixture: 1 to 90%, preferably 5 to 20% -   surfactant: 1 to 30%, preferably 10 to 20% -   liquid carrier: 5 to 94%, preferably 70 to 85%     Dusts: -   active ingredient mixture: 0.1 to 10%, preferably 0.1 to 5% -   solid carrier: 99.9 to 90%, preferably 99.9 to 99%     Suspension Concentrates: -   active ingredient mixture: 5 to 75%, preferably 10 to 50% -   water: 94 to 24%, preferably 88 to 30%, -   surfactant: 1 to 40%, preferably 2 to 30%     Wettable powders: -   active ingredient mixture: 0.5 to 90%, preferably 1 to 80% -   surfactant: 0.5 to 20%, preferably 1 to 15% -   solid carrier: 5 to 95%, preferably 15 to 90%     Granules: -   active ingredient mixture: 0.1 to 30%, preferably 0.1 to 15% -   solid carrier: 99.5 to 70%, preferably 97 to 85%

The following Examples illustrate the invention further, but do not limit the invention.

Formulation Examples for mixtures of herbicides of formula I, optionally of formulae 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, Pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin and safeners of formulae 3.1 to 3.17 (%=percent by weight) F1. Emulsifiable concentrates a) b) c) d) active ingredient mixture  5% 10% 25% 50% calcium dodecylbenzenesulfonate  6%  8%  6% 8% castor oil polyglycol ether  4% —  4% 4% (36 mol of ethylene oxide) octylphenol polyglycol ether —  4% — 2% (7-8 mol of ethylene oxide) cyclohexanone — — 10% 20% arom. hydrocarbon mixture 85% 78% 55% 16% C₉-C₁₂

Emulsions of any desired concentration can be obtained from such concentrates by dilution with water. F2. Solutions a) b) c) d) active ingredient mixture  5% 10% 50% 90% 1-methoxy-3-(3-methoxy- — 20% 20% — propoxy)-propane polyethylene glycol MW 400 20% 10% — — N-methyl-2-pyrrolidone — — 30% 10% arom. hydrocarbon mixture 75% 60% — — C₉-C₁₂

The solutions are suitable for use in the form of microdrops. F3. Wettable powders a) b) c) d) active ingredient mixture  5% 25% 50% 80% sodium lignosulfonate  4% —  3% — sodium lauryl sulfate  2%  3% —  4% sodium diisobutylnaphthalene- —  6%  5%  6% sulfonate octylphenol polyglycol ether —  1%  2% — (7-8 mol of ethylene oxide) highly dispersed silicic acid  1%  3%  5% 10% kaolin 88% 62% 35% —

The active ingredient is mixed thoroughly with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of any desired concentration. F4. Coated granules a) b) c) active ingredient mixture 0.1% 5% 15% highly dispersed silicic acid 0.9% 2% 2% inorganic carrier 99.0% 93% 83% (diameter 0.1-1 mm) e.g. CaCO₃ or SiO₂

The active ingredient is dissolved in methylene chloride and applied to the carrier by spraying, and the solvent is then evaporated off in vacuo. F5. Coated granules a) b) c) active ingredient mixture 0.1% 5% 15% polyethylene glycol MW 200 1.0% 2% 3% highly dispersed silicic acid 0.9% 1% 2% inorganic carrier 98.0% 92% 80% (diameter 0.1-1 mm) e.g. CaCO₃ or SiO₂

The finely ground active ingredient is uniformly applied, in a mixer, to the carrier moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner. F6. Extruder granules a) b) c) d) active ingredient mixture 0.1% 3% 5% 15% sodium lignosulfonate 1.5% 2% 3% 4% carboxymethylcellulose 1.4% 2% 2% 2% kaolin 97.0% 93% 90% 79%

The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air. F7. Dusts a) b) c) active ingredient mixture 0.1% 1% 5% talcum 39.9% 49% 35% kaolin 60.0% 50% 60%

Ready-to-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture in a suitable mill. F8. Suspension concentrates a) b) c) d) active ingredient mixture   3%  10%  25%  50% ethylene glycol   5%   5%   5%   5% nonylphenol polyglycol ether —   1%   2% — (15 mol of ethylene oxide) sodium lignosulfonate   3%   3%   4%   5% carboxymethylcellulose   1%   1%   1%   1% 37% aqueous formaldehyde 0.2% 0.2% 0.2% 0.2% solution silicone oil emulsion 0.8% 0.8% 0.8% 0.8% water  87%  79%  62%  38%

The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.

It is often more practical for the compounds of formulae I, 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin and 3.1 to 3.17 to be formulated separately and then to be brought together in the desired mixing ratio in the applicator in the form of a “tank mixture” in water shortly before application.

The ability of the safeners of formulae 3.1 to 3.17 to protect crop plants against the phytotoxic action of herbicides of formula I is illustrated in the following Examples.

Biological Example: Safening Action

The test plants are grown in plastics pots under greenhouse conditions to the 4-leaf stage. At that stage, either the herbicides alone or the mixtures of the herbicides with the test compounds being tested as safeners are applied to the test plants. The test compounds are applied in the form of an aqueous suspension prepared from a 25% wettable powder (Example F3, b)), using 500 litres of water/ha. 4 weeks after application, the phytotoxic action of the herbicides on the crop plants, e.g. maize and cereals, is evaluated using a percentage scale. 100% indicates that the test plant has died, 0% indicates no phytotoxic action. The mixtures according to the invention exhibit a good action in this test. 

1. A selectively herbicidal composition that, in addition to comprising customary inert formulation adjuvants, comprises as active ingredient a mixture of a) a herbicidally effective amount of the compound of formula I

wherein p is 0 or 1; R₁ is a C₁-C₆alkylene, C₃-C₆alkenylene or C₃-C₆alkynylene chain, which may be substituted one or more times by halogen or by R₅, the unsaturated bonds of the chain not being attached directly to the substituent X₁; X₁ is oxygen, —O(CO)—, —(CO)O—, —O(CO)O—, —N(R₆)—O—, —O—NR₅₁-, thio, sulfinyl, sulfonyl, —SO₂NR₇—, —NR₅₂SO₂— or —NR₈—; R₂ is a C₁-C₈alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which is substituted one or more times by halogen, hydroxy, amino, formyl, nitro, cyano, mercapto, carbamoyl, C₁-C₆alkoxy, C₁-C₆alkoxycarbonyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆-cycloalkyl, halo-substituted C₃-C₆cycloalkyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, C₁-C₆halo-alkoxy, C₃-C₆haloalkenyloxy, cyano-C₁-C₆alkoxy, C₁-C₆alkoxy-C₁-C₆alkoxy, C₁-C₆alkoxy-C₁-C₆alkoxy-C₁-C₆alkoxy, C₁-C₆alkylthio-C₁-C₆alkoxy, C₁-C₆alkylsulfinyl-C₁-C₆alkoxy, C₁-C₆-alkylsulfonyl-C₁-C₆alkoxy, C₁-C₆alkoxycarbonyl-C₁-C₆alkoxy, C₁-C₆alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, oxiranyl (which may in turn be substituted by C₁-C₆alkyl), (3-oxetanyl)-oxy (which may in turn be substituted by C₁-C₆alkyl), benzylthio, benzylsulfinyl, benzylsulfonyl, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino, R₉S(O)₂O, R₁₀N(R₁₁)SO₂—, rhodano, phenyl, phenoxy, phenylthio, phenylsulfinyl or by phenylsulfonyl; wherein the phenyl- or benzyl-containing groups may in turn be substituted by one or more C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or nitro groups, or R₂ is phenyl, which may be substituted one or more times by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; or R₂ is C₃-C₆cycloalkyl; C₃-C₆cycloalkyl substituted by C₁-C₆alkoxy or by C₁-C₆alkyl; 3-oxetanyl or 3-oxetanyl substituted by C₁-C₆alkyl; or, when Q is Q₂ or Q₃, or when Q is Q₁ wherein R₁₄ and R₂₂ denote a C₂-C₃alkylene chain, R₂ may additionally be a five- to ten-membered, monocyclic or fused bicyclic ring system, which may be aromatic, saturated or partially saturated and which may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system being bonded to the substituent X₁ directly or via a C₁-C₄alkylene, C₂-C₄alkenyl-C₁-C₄alkylene, C₂-C₄alkynyl-C₁-C₄alkylene, —N(R₁₂)—C₁-C₄alkylene, —SO—C₁-C₄alkylene or —SO₂—C₁-C₄alkylene group, and wherein each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms and the ring system may itself be mono-, di- or tri-substituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₁-C₆alkoxy, hydroxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano, nitro, phenyl or by benzylthio, wherein phenyl and benzylthio may in turn be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen; or R₂ is hydrogen or unsubstituted C₁-C₈alkyl, when either a) R₁ is substituted by the group R₅, or b) Q is the group Q₂, or c) Q is the group Q₃ when X₁ is —O(CO)—, —(CO)O—, —N(R₆)—O—, —O—NR₅₁—, —SO₂NR₇—, —NR₅₂SO₂— or —NR₈—; or d) Q is the group Q₁ when X₁ is —N(R₆)—O—, —O—NR₅₁—, —SO₂NR₇—, —NR₅₂SO₂— or —NR₈—, or e) Q is the group Q₁ wherein R₁₄ and R₂₂ in Q₁ denote a C₂-C₃alkylene chain and X₁ is —O(CO)— or —(CO)O—; R₃ is C₁-C₃haloalkyl; R₄ is hydrogen, halogen, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃alkoxy-C₁-C₃alkyl or C₁-C₃alkoxy-C₁-C₃alkoxy; R₅ is hydroxy, C₁-C₆alkoxy, C₃-C₆cycloalkyloxy, C₁-C₆alkoxy-C₁-C₆alkoxy, C₁-C₆alkoxy-C₁-C₆alkoxy-C₁-C₆alkoxy or C₁-C₂alkylsulfonyloxy; R₆, R₇, R₈, R₉, R₁₀, R₁₁, R₁₂, R₅₁ and R₅₂ are each independently of the others hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkyl substituted by C₁-C₆alkoxy, benzyl, or phenyl, wherein phenyl and benzyl may in turn be substituted one or more times by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆-alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; wherein R₆ is not hydrogen when R₉ is hydrogen, C₁-C₆alkoxycarbonyl or C₁-C₆alkylcarbonyl; Q is Q₁

wherein A₁ is C(R₁₄R₁₅), NR₁₆ or oxygen; A₂ is C(R₁₇R₁₈), C(O), —C═N—O—R₁₉, oxygen, thio, sulfinyl, sulfonyl, —NR₂₀ or ethylene; with the provisos that A₁ is other than oxygen when A₂ is oxygen, C(O), thio, sulfinyl, —C═N—O—R₁₉, NR₂₀ or C(R₁₇R₁₈), R₁₇ and R₁₈ being each independently of the other C₁-C₄alkoxy, C₁-C₄-alkylthio, C₁-C₄alkylsulfinyl or C₁-C₄alkylsulfonyl; and that Al is other than NR₁₆ when A₂ is thio, sulfinyl or C(R₁₇R₁₈), R₁₇ and R₁₈ being each independently of the other C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or C₁-C₄alkylsulfonyl; R₁₄ and R₂₂ are each independently of the other hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₄-alkenyl, C₃-C₄alkynyl, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylsulfonyl-oxy, C₁-C₄alkoxy, C₁-C₄alkoxycarbonyl or C₁-C₄alkylcarbonyl; R₁₅ and R₂₁ are each independently of the other hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₄-alkenyl or C₃-C₄alkynyl; R₁₇ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or C₁-C₄alkylsulfonyl; R₁₈ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl, C₁-C₄alkoxy, C₁-C₄-alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl or di(C₁-C₄)alkoxyalkyl-C₁-C₄alkyl; R₂₀ is C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl, C₁-C₄alkylcarbonyl, C₁-C₄alkyl-carbonyloxy, di(C₁-C₄)alkylaminocarbonyl or benzyl, wherein the phenyl group may be substituted one or more times by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; R₁₉ and R₁₆ are each independently of the other hydrogen, C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl, benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted one or more times by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; or R₁₄ and R₂₂ together form a C₂-C₃alkylene chain; or R₁₄ and R₁₅ together and/or R₁₇ and R₁₈ together and/or R₂₁ and R₂₂ together form a C₂-C₄alkylene chain, which may be interrupted by oxygen and/or by carbonyl and/or by sulfur, with the proviso that the oxygen and sulfur atoms are separated by at least one methylene group; or R₁₄ and R₁₈ together form a C₂-C₄alkylene chain; or R₂₂ and R₁₈ together form a C₂-C₄alkylene chain; or R₁₈ forms, together with R₂₂ or R₁₄, a direct bond; or R₁₆ and R₁₈ together form a C₂-C₄alkylene chain; R₁₃ is hydroxy; O⁻M⁺ wherein M⁺ is an alkali metal cation or an ammonium cation; halogen, C₁-C₁₂alkylsulfonyloxy, amino, C₁-C₄alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂-haloalkylthio, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₃-C₁₂alkenylthio, C₃-C₁₂-alkenylsulfinyl, C₃-C₁₂alkenylsulfonyl, C₃-C₁₂alkynylthio, C₃-C₁₂alkynylsulfinyl, C₃-C₁₂alkynyl-sulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl, C₁-C₄-alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₂₃R₂₄N, R₂₅R₂₆NNH, R₂₇R₂₈NC(O)O—, R₂₉R₃₀NC(O)NH—, C₁-C₁₈alkyl-carbonyloxy, C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyl-oxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy or C₁-C₁₂alkylthiocarbamoyl, wherein the alkyl, alkenyl and alkynyl groups may be substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl or by cyano; or R₁₃ is phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenyl-sulfonyloxy or benzoyloxy, wherein the phenyl groups may in turn be substituted by one or more halogen, nitro, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy or C₁-C₄haloalkoxy groups; or R₁₃ is a group Het₁-thio, Het₂-sulfinyl, Het₃-sulfonyl, Het₄-(CO)O or Het₅-N(R₃₃); wherein Het₁, Het₂, Het₃, Het₄ and Het₅ are each independently of the others a five- to ten-membered, monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and which may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur and wherein each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms and the ring system may itself be substituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, di(C₁-C₄alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano, nitro or by phenyl, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen; R₂₃, R₂₄, R₂₅, R₂₆, R₂₇, R₂₈, R₂₉, R₃₀ and R₃₃ are each independently of the others hydrogen or C₁-C₆alkyl; or R₂₃ and R₂₄ together or R₂₅ and R₂₆ together or R₂₇ and R₂₈ together or R₂₉ and R₃₀ together are pyrrolidino, piperidino, morpholino or thiomorpholino, each of which may be mono- or poly-substituted by methyl groups; or Q is Q₂

wherein R₃₄ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl, C₂-C₄alkenyl, C₂-C₄alkynyl or benzyl, wherein the phenyl group may be substituted one or more times by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; R₃₅ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl or benzyl, wherein the phenyl group may be substituted one or more times by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; R₃₆ is hydroxy; O⁻M⁺ wherein M⁺ is an alkali metal cation or an ammonium cation; halogen, C₁-C₁₂alkylsulfonyloxy, amino, C₁-C₄alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkyl-thio, C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₃-C₁₂alkenylthio, C₃-C₁₂alkenylsulfinyl, C₃-C₁₂alkenylsulfonyl, C₃-C₁₂alkynylthio, C₃-C₁₂alkynylsulfinyl, C₃-C₁₂alkynylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄alkyl-sulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₃₇R₃₈N, R₃₉R₄₀NNH, R₄₁R₄₂NC(O)O—, R₄₃R₄₄NC(O)NH—, C₁-C₁₈alkylcarbonyloxy, C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyl-oxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy or C₁-C₁₂alkylthiocarbamoyl, wherein the alkyl, alkenyl and alkynyl groups may be substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl or by cyano; or R₃₆ is phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenyl-sulfonyloxy or benzoyloxy, wherein the phenyl groups may in turn be substituted one or more times by halogen, nitro, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy or by C₁-C₄halo-alkoxy, or R₃₆ is a group Het₇-thio, Het₈-sulfinyl, Het₉-sulfonyl, Het₁₀-(CO)O or Het₁₁—N(R₄₇); wherein Het₇, Het₈, Het₉, Het₁₀ and Het₁₁ are each independently of the others a five- to ten-membered, monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and which may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur and wherein each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms and the ring system may itself be substituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkyl-sulfonyl, di(C₁-C₄alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano, nitro or by phenyl, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen; R₃₇, R₃₈, R₃₉, R₄₀, R₄₁, R₄₂, R₄₃, R₄₄ and R₄₇ are each independently of the others hydrogen or C₁-C₆alkyl; or R₃₇ and R₃₈ together or R₃₉ and R₄₀ together or R₄₁ and R₄₂ together or R₄₃ and R₄₄ together are pyrrolidino, piperidino, morpholino or thiomorpholino, each of which may be mono- or poly-substituted by methyl groups; or Q is Q₃

wherein R₄₉ is C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl or halo-substituted C₃-C₆cycloalkyl; R₅₀ is C₁-C₃alkylene, which may be substituted by halogen, hydroxy, C₁-C₆alkoxy, C₂-C₈-alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy-C₁-C₆alkoxy, C₁-C₆alkoxy-C₁-C₆alkoxy-C₁-C₆alkoxy, (3-oxetanyl)-oxy, or by (3-oxetanyl)-oxy substituted by C₁-C₆alkyl, or by benzylthio, benzylsulfinyl, benzylsulfonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or by phenylsulfonyl, wherein the phenyl- and benzyl-containing groups may in turn be substituted by one or more C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or nitro groups; or R₅₀ is phenyl, wherein the phenyl-containing group may in turn be substituted by one or more C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, halogen, cyano, hydroxy or nitro substituents, or R₅₀ is C₃-C₆cycloalkyl, C₃-C₆cycloalkyl substituted by C₁-C₆alkoxy or by C₁-C₆alkyl, 3-oxetanyl or 3-oxetanyl substituted by C₁-C₆alkyl; and n is 0, 1 or 2; or an agronomically acceptable salt/N-oxide/isomer/enantiomer of such a compound except for the compound 4-hydroxy-3-[2-(2-methoxyethoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonyl]-bicyclo[3.2.1]oct-3-en-2-one, and with the provisos that —R₁—X₁—R₂ is other than C₁-C₄alkoxy-C₁-C₄alkoxy-C₁-C₄alkyl when a) Q is Q₁ wherein A₁ is C(R₁₄R₁₅) and A₂ is C(R₁₇R₁₈), R₁₅, R₁₇ and R₁₈ are hydrogen and R₁₄ and R₂₂ together form a C₂-C₃alkylene chain; and when b) Q is Q₁, R₁₄ and R₂₂ do not together form a C₂-C₃alkylene chain, A₁ is C(R₁₄R₁₅), or A₁ is NR₁₆ and A₂ is oxygen; and when c) Q is Q₃, and b) a synergistically effective amount of one or more compounds selected from a compound of formula 2.1

wherein R₅₁ is CH₂—OMe, ethyl or hydrogen; R₅₂ is hydrogen, or R₅₁ and R₅₂ together are the group —CH═CH—CH═CH—; and a compound of formula 2.2

wherein R₅₃ is ethyl, R₅₄ is methyl or ethyl, and R₅₅ is —CH(Me)—CH₂OMe, <S>—CH(Me)—CH₂OMe, CH₂OMe or CH₂O—CH₂CH₃; and a compound of formula 2.3

wherein R₅₆ is CH(Me)—CH₂OMe or <S>CH(Me)—CH₂OMe; and a compound of formula 2.4

wherein R₅₇ is chlorine, methoxy or methylthio, R₅₈ is ethyl or isopropyl, and R₅₉ is ethyl, isopropyl, —C(CN)(CH₃)—CH₃ or tert-butyl; and a compound of formula 2.5

wherein R₆₀ is ethyl or n-propyl, R₆₁ is COO⁻½ Ca⁺⁺, —CH₂—CH(Me)S—CH₂CH₃, the group

or the group

and X is oxygen, N—O—CH₂CH₃ or N—O—CH₂CH═CH—Cl; and a compound of formula 2.6

wherein R₆₂ is hydrogen, methoxy or ethoxy, R₆₃ is hydrogen, methyl, methoxy or fluorine, R₆₄ is COOMe, fluorine or chlorine, R₆₅ is hydrogen or methyl, Y is methine, C—F or nitrogen, Z is methine or nitrogen, and R₆₆ is fluorine or chlorine; and a compound of formula 2.7

wherein R₆₇ is hydrogen or —C(O)—S-n-octyl; and a compound of formula 2.8

wherein R₆₈ is either bromine or iodine; and a compound of formula 2.9

wherein R₆₉ is chlorine or nitro; and a compound of formula 2.10

wherein R₇₀ is fluorine or chlorine, and R₇₁ is —CH₂—CH(Cl)—COOCH₂CH₃ or —NH—SO₂Me; and a compound of formula 2.11

wherein R₇₂ is trifluoromethyl or chlorine; and a compound of formula 2.12

wherein R₇₃ is NH₂ or <S>NH₂; and a compound of formula 2.13

wherein Y₂ is nitrogen, methine, C—NH—CHO, C—CH₂—NH—SO₂CH₃ or N-Me, Y₁ is nitrogen, methine, C—Cl or C—I, Y₃ is methine, Y₄ is methine or Y₃ and Y₄ together are sulfur or C—Cl, Y₅ is nitrogen or methine, Y₆ is methyl, difluoromethoxy, trifluoromethyl or methoxy, Y₇ is methoxy or difluoromethoxy and R₇₄ is CONMe₂, COOMe, COOC₂H₅, trifluoromethyl, CH₂—CH₂CF₃, O—CH₂—CH₂Cl or SO₂CH₂CH₃, or a sodium salt thereof; and the compound of formula 2.13.c

and the compound of formula 2.14

and the compound of formula 2.15

and the compound of formula 2.16

and ammonium, isopropylammonium, sodium and trimesium salts thereof; and the compound of formula 2.17

and the compound of formula 2.18

and the compound of formula 2.19

and the compound of formula 2.20

and the compound of formula 2.21

and the compound of formula 2.22

and the compound of formula 2.23

and the compound of formula 2.24

and the compound of formula 2.25

and the compound of formula 2.26

and the compound of formula 2.27

and the compound of formula 2.28

the compound of formula 2.29

and the compound of formula 2.30

and the compound of formula 2.31

and the compound of formula 2.32

and the compound of formula 2.33

and the compound of formula 2.34

and the compound of formula 2.35

and the compound of formula 2.36

and the compound of formula 2.37

and the compound of formula 2.38

and the compound of formula 2.39

and the compound of formula 2.40

and the compound of formula 2.41

and the compound of formula 2.42

and the compound of formula 2.43

and the compound of formula 2.44

and the compound of formula 2.45

and the compound of formula 2.46

and the compound of formula 2.47

and the compound of formula 2.48

and the compound of formula 2.49

and the compound of formula 2.50

and the compound of formula 2.51

and a compound of formula 2.52

wherein R₀₁, R₀₂ and R₀₃ are each independently of the others halogen, nitro, cyano, C₁-C₄alkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, C₁-C₄haloalkyl, C₂-C₆haloalkenyl, C₃-C₆cycloalkyl, halo-substituted C₃-C₆cycloalkyl, C₁-C₆alkoxyalkyl, C₁-C₆alkylthioalkyl, hydroxy, mercapto, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, amino, C₁-C₄alkylamino or di(C₁-C₄alkyl)amino; R₀₄ and R₀₅ together are a group —C—R₀₆(R₀₇)—O—C—R₀₈(R₀₉)—C—R₀₁₀(R₀₁₁)—C—R₀₁₂(R₀₁₃)—  (Z₁), —C—R₀₁₄(R₀₁₅)—C—R₀₁₆(R₀₁₇)—O—C—R₀₁₈(R₀₁₉)—C—R₀₂₀(R₀₂₁)—  (Z₂) or —C—R₀₂₂(R₀₂₃)—C—R₀₂₄(R₀₂₅)—C—R₀₂₆(R₀₂₇)—O—C—R₀₂₈(R₀₂₉)—  (Z₃), wherein R₀₆, R₀₇, R₀₈, R₀₉, R₀₁₀, R₀₁₁, R₀₁₂, R₀₁₃, R₀₁₄, R₀₁₅, R₀₁₆, R₀₁₇, R₀₁₈, R₀₁₉, R₀₂₀, R₀₂₁, R₀₂₂, R₀₂₃, R₀₂₄, R₀₂₅, R₀₂₆, R₀₂₇, R₀₂₈ and R₀₂₉ are, each independently of the others, hydrogen, halogen, C₁-C₄alkyl or C₁-C₄haloalkyl, it being possible for an alkylene ring, which together with the carbon atoms of the group Z₁, Z₂ or Z₃ contains from 2 to 6 carbon atoms and which may be interrupted by oxygen, to be either fused or spiro-bound to the carbon atoms of the group Z₁, Z₂ or Z₃ or that alkylene ring bridges at least one ring atom of the group Z₁, Z₂ or Z₃; G is hydrogen, —C(X₁)—R₀₃₀, —C(X₂)—X₃—R₀₃₁, —C(X₄)—N(R₀₃₂)—R₀₃₃, —SO₂—R₀₃₄, an alkali metal cation, alkaline earth metal cation, sulfonium cation or ammonium cation or —P(X₅)(R₀₃₅)—R₀₃₆; X₁, X₂, X₃, X₄ and X₅ are each independently of the others oxygen or sulfur; and R₀₃₀, R₀₃₁, R₀₃₂, R₀₃₃, R₀₃₄, R₀₃₅ and R₀₃₆ are each independently of the others hydrogen, C₁-C₅alkyl, C₁-C₅haloalkyl, C₂-C₅alkenyl, C₁-C₅alkoxyalkyl, C₃-C₆cycloalkyl or phenyl, and R₀₃₄ may additionally be C₂-C₂₀alkenyl; C₂-C₂₀alkenyl substituted by halogen, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyloxy, C₁-C₆alkoxy, C₁-C₆thioalkyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkylcarbonylthio, C₁-C₆alkylsulfonyl, C₁-C₆alkylsulfoxyl, C₁-C₆alkylaminosulfonyl, C₁-C₆(di)alkylaminosulfonyl, C₁-C₆C₁-C₆alkylsulfonyloxy, C₁-C₆alkyl-sulfonylamino, C₁-C₆alkylamino, C₁-C₆(di)alkylamino, C₁-C₆alkylcarbonylamino, di-C₁-C₆ alkylcarbonylamino, C₁-C₆alkylalkylcarbonylamino, cyano, (C₃-C₇)cycloalkyl, (C₃-C₇)heterocyclyl, tri-C₁-C₆alkylsilyl, tri-C₁-C₆alkylsilyloxy, phenyl or heteroaryl; or R₀₃₄ is C₂-C₂₀alkynyl; C₂-C₂₀alkynyl substituted by halogen, C₁-C₆alkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbonyloxy, C₁-C₆alkoxy, C₁-C₆thioalkyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkylcarbonylthio, C₁-C₆alkylsulfonyl, C₁-C₆alkylsulfoxyl, C₁-C₆alkylaminosulfonyl, di-C₁-C₆ alkylaminosulfonyl, C₁-C₆alkylsulfonyloxy, C₁-C₆alkylsulfonylamino, C₁-C₆alkylamino, di-C₁-C₆alkylamino, C₁-C₆alkylcarbonylamino, di-C₁-C₆alkylcarbonylamino, C₁-C₆alkylcarbonylamino, cyano, (C₃-C₇)cycloalkyl, (C₃-C₇)heterocyclyl, tri-C₁-C₆alkylsilyl, tri-C₁-C₆alkylsilyloxy, phenyl or heteroaryl; or R₀₃₄ is (C₁-C₇)cycloalkyl; (C₁-C₇)cycloalkyl substituted by halogen, haloalkyl, C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylcarbonyloxy, C₁-C₆thioalkyl, C₁-C₆alkylcarbonylthio, C₁-C₆alkylamino, C₁-C₆alkylcarbonylamino, tri-C₁-C₆alkylsilyl or by tri-C₁-C₆alkylsilyloxy; or R₀₃₄ is heteroaryl; heteroaryl substituted by halogen, C₁-C₆haloalkyl, nitro, cyano, C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylcarbonyloxy, C₁-C₆thioalkyl, C₁-C₆alkylcarbonylthio, C₁-C₆alkylamino, C₁-C₆alkylcarbonylamino, tri-C₁-C₆alkylsilyl or by tri-C₁-C₆alkylsilyloxy; heteroaryloxy, heteroarylthio, heteroarylamino, di-heteroarylamino, phenylamino, diphenylamino, C₂-C₆cycloalkylamino, di-C₂-C₆cycloalkylamino or C₂-C₆cycloalkoxy and salts and diastereoisomers of compounds of formula 2.52; and the compound of formula 2.53

and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin.
 2. A method of controlling undesired plant growth in crops of useful plants, which comprises allowing a herbicidally effective amount of a composition according to claim 1 to act on the crop plant or the area of cultivation thereof.
 3. A method according to claim 2, wherein the crop plant is maize or a cereal.
 4. A method according to claim 2, wherein the crop of useful plants is treated with the said composition at a rate of application corresponding to a total amount of active ingredient of from 1 to 5000 g per hectare.
 5. A selectively herbicidal composition that, in addition to comprising customary inert formulation adjuvants, such as carriers, solvents and wetting agents, comprises as active ingredient a mixture of a) an amount, effective for herbicide synergism, of the compound of formula I according to claim 1 and one or more compounds selected from the compounds of formulae 2.1 to 2.53 and the compounds prosulfocarb, picolinafen, pyraflufen-ethyl, beflubutamid, fenoxaprop-P-ethyl, diclofop-methyl, amidosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, imazamethabenz-methyl, flucarbazone, chlorotoluron, isoproturon, methabenzthiazuron, bifenox, fluoroglycofen-ethyl, imazosulfuron, diflufenican, bilanafos, ethalfluralin, trifluralin, fluthiamide, isoxaben, triallate, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, MCPP, mecoprop-P, clopyralid, fluroxypyr, quinmerac, benazolin-ethyl, difenzoquat, cyhalofop-butyl, dithiopyr, quinclorac, prodiamine, benefin and trifluralin according to claim 1 and b) an amount, effective for herbicide antagonism, of a compound selected from the compound of formula 3.1

and the compound of formula 3.2

and the compound of formula 3.3

the free acid thereof or a hydrate or salt thereof, and the compound of formula 3.4

and the compound of formula 3.5

and the compound of formula 3.6

and the compound of formula 3.7

and the compound of formula 3.8

and of formula 3.9 Cl₂CHCON(CH₂CH═CH₂)₂  (3.9), and of formula 3.10

and of formula 3.11

and of formula 3.12

or a methyl or ethyl ester thereof or a salt thereof, and of formula 3.13

and of formula 3.14

and of formula 3.15

and of formula 3.16

and of formula 3.17


6. A method for the selective control of weeds and grasses in crops of useful plants, which comprises treating the useful plants, seeds or cuttings thereof, or the area of cultivation thereof, with an amount, effective for herbicide synergism, of a composition according to claim
 5. 7. A method according to claim 6, wherein the rate of application of herbicide is from 1 to 5000 g/ha and the rate of application of safener is from 0.001 to 0.5 kg/ha.
 8. A method according to claim 6, wherein the crop of useful plants is maize or a cereal.
 9. A selectively herbicidal composition that, in addition to comprising customary inert formulation adjuvants, such as carriers, solvents and wetting agents, comprises as active ingredient a mixture of a) a herbicidally effective amount of a compound of formula I according to claim 1 and b) an amount, effective for herbicide antagonism, of a compound selected from the compound of formula 3.1

and the compound of formula 3.2

and the compound of formula 3.3

the free acid thereof or a salt or hydrate thereof, and the compound of formula 3.4

and the compound of formula 3.5

and the compound of formula 3.6

and the compound of formula 3.7

and the compound of formula 3.8

and of formula 3.9 Cl₂CHCON(CH₂CH═CH₂)₂  (3.9), and of formula 3.10

and of formula 3.11

and of formula 3.12

or a methyl or ethyl ester thereof or a salt thereof, and of formula 3.13

and of formula 3.14

and of formula 3.15

and of formula 3.16

and of formula 3.17


10. A method for the selective control of weeds and grasses in crops of useful plants, which comprises treating the useful plants, seeds or cuttings thereof, or the area of cultivation thereof, with a selective herbicidal amount of a composition according to claim
 9. 